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Supplementary material:
Supplementary File 1 (MOL, 2 KiB)
Supplementary File 2 (INCHI, 431 B)
Supplementary File 3 (MOL, 2 KiB)
Supplementary File 4 (PDF, 1162 KiB)

7 pages, 1926 KiB

Open AccessShort Note

6-Hydroxy-2-methylbenzofuran-4-carboxylic Acid

by Matteo Mori, Fiorella Meneghetti, Laurent R. Chiarelli, Alessia Diego, Donatella Nava, Arianna Gelain, Giulia Cazzaniga, Stefania Villa and Elena Pini

Molbank 2020, 2020(2), M1143; https://doi.org/10.3390/M1143 - 18 Jun 2020

Viewed by 2330

Abstract

6-Hydroxy-2-methylbenzofuran-4-carboxylic acid was synthesized in two steps, starting from 3,5-dihydroxybenzoate. The product was obtained through a direct thermal one-pot cyclization with propargyl bromide, followed by a base-catalyzed hydrolysis. Its molecular structure was elucidated by means of mono- and bidimensional NMR techniques, ESI-MS, FT-IR [...] Read more.

(This article belongs to the Section Structure Determination)

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Figure 1

Supplementary material:
Supplementary File 1 (PDF, 779 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 800 B)
Supplementary File 4 (MOL, 2 KiB)

5 pages, 1170 KiB

Open AccessShort Note

4′-(N-(Propan-1,2-dienyl)pyrrol-2-yl)-2,2′:6′,2″-terpyridine

by Jérôme Husson and Laurent Guyard

Molbank 2020, 2020(2), M1142; https://doi.org/10.3390/M1142 - 10 Jun 2020

Cited by 5 | Viewed by 2381

Abstract

A new pyrrole-substituted terpyridine derivative that possesses an allene moiety was obtained as an “unexpected” sole product during an attempt to alkylate the N-atom of pyrrole with propargyl bromide in order to obtain an alkyne-functionalized terpyridine. Full article

(This article belongs to the Collection Molecules from Side Reactions)

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Graphical abstract

Supplementary material:
Supplementary File 1 (MOL, 3 KiB)
Supplementary File 2 (INCHI, 2 KiB)
Supplementary File 3 (MOL, 3 KiB)
Supplementary File 4 (7Z, 832 KiB)

5 pages, 3185 KiB

Open AccessCommunication

Synthesis, Structure and Hirshfeld Surface Analysis of Phosphine–Imidazolium Salt

by Alexey V. Smarun, Violeta Jevtovic and Rakesh Ganguly

Molbank 2020, 2020(2), M1141; https://doi.org/10.3390/M1141 - 08 Jun 2020

Cited by 1 | Viewed by 1931

Abstract

In the field of homogeneous catalysis, particularly in anti-Markovnikov hydration, sterically demanding phosphine ligand has found to be very effective. Here we report the crystal structure of a phosphine-imidazolium salt which crystallized in monoclinic space group P_21/c with a = 16.6623(13) (Å), b = 10.6686(8) (Å) and c = 12.8916(11) with = 110.232(2). Hirshfeld surface analysis show that the halogen–hydrogen interaction leads to a formation of 1D chain. Full article

(This article belongs to the Section Structure Determination)

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Figure 1

Supplementary material:
Supplementary File 1 (PDF, 1504 KiB)
Supplementary File 2 (MOL, 1 KiB)
Supplementary File 3 (INCHI, 405 B)
Supplementary File 4 (MOL, 1 KiB)
Supplementary File 5 (MOL, 4 KiB)
Supplementary File 6 (INCHI, 1 KiB)
Supplementary File 7 (MOL, 4 KiB)
Supplementary File 8 (MOL, 2 KiB)
Supplementary File 9 (INCHI, 543 B)
Supplementary File 10 (MOL, 2 KiB)

5 pages, 586 KiB

Open AccessFeature PaperShort Note

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

by Jack Bennett and Paul V. Murphy

Molbank 2020, 2020(2), M1140; https://doi.org/10.3390/M1140 - 03 Jun 2020

Viewed by 2368

Abstract

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by ¹H and ¹³C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Scheme 1

Supplementary material:
Supplementary File 1 (PDF, 650 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 488 B)
Supplementary File 4 (MOL, 2 KiB)
Supplementary File 5 (MOL, 2 KiB)
Supplementary File 6 (INCHI, 488 B)
Supplementary File 7 (MOL, 2 KiB)

6 pages, 887 KiB

Open AccessCommunication

Synthesis of (R) and (S)-3-Chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones

by Andreas S. Kalogirou, Christopher R. M. Asquith and Panayiotis A. Koutentis

Molbank 2020, 2020(2), M1139; https://doi.org/10.3390/M1139 - 01 Jun 2020

Cited by 2 | Viewed by 2442

Abstract

The reaction of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one with (R) and (S)-1,3-dimethylpiperazines (1 equiv), in THF, at ca. 20 °C gives (R) and (S)-3-chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones in 70% and 68% yields, respectively. The new compounds were fully characterized. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Figure 1

Supplementary material:
Supplementary File 1 (MOL, 4 KiB)
Supplementary File 2 (INCHI, 1 KiB)
Supplementary File 3 (MOL, 3 KiB)
Supplementary File 4 (PDF, 308 KiB)

7 pages, 681 KiB

Open AccessCommunication

9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity

by Giovanni Ribaudo, Alberto Ongaro, Erika Oselladore, Giuseppe Zagotto, Maurizio Memo and Alessandra Gianoncelli

Molbank 2020, 2020(2), M1138; https://doi.org/10.3390/M1138 - 22 May 2020

Cited by 1 | Viewed by 2494

Abstract

G-quadruplex DNA is the target of several natural and synthetic small molecules with antiproliferative and antiviral activity. We here report the synthesis through Sonogashira reaction and A3 coupling of a disubstituted anthracene derivative, 9,10-bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene. The binding of this compound to G-quadruplex and double stranded DNA sequences was evaluated using electrospray ionization mass spectrometry (ESI-MS), demonstrating selectivity for the first structure. The interaction pattern of the ligand with G-quadruplex was investigated by molecular docking and stacking was found to be the preferred binding mode. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 241 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 524 B)
Supplementary File 4 (MOL, 2 KiB)

4 pages, 352 KiB

Open AccessShort Note

1-Benzyl-2-(thien-2-yl)-4,5-dihydro-1H-imidazole

by Alexandra S. Golubenkova, Nikita E. Golantsov, Alexey A. Festa and Leonid G. Voskressensky

Molbank 2020, 2020(2), M1137; https://doi.org/10.3390/M1137 - 18 May 2020

Cited by 2 | Viewed by 2291

Abstract

Imidazolines are a valuable class of organic compounds, namely ligands of imidazoline receptors, chiral ligands for metal catalysis, synthetic intermediates. The title compound has been prepared through a modified procedure, employing N-benzylethylenediamine and thiophene-2-carbaldehyde under the action of N-bromosuccinimide (NBS) in [...] Read more.

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Supplementary material:
Supplementary File 1 (ZIP, 287 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 723 B)
Supplementary File 4 (MOL, 2 KiB)

4 pages, 332 KiB

Open AccessShort Note

4-(3-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)thieno[3,2-d]pyrimidine

by Eun Sun Noh, Sung Min Kim and Yang-Heon Song

Molbank 2020, 2020(2), M1136; https://doi.org/10.3390/M1136 - 17 May 2020

Cited by 2 | Viewed by 2211

Abstract

A new hybrid compound, 4-(3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)thieno[3,2-d]pyrimidine 3, with promising biological activity was efficiently synthesized by the reaction of 3-phenyl-1-(thieno[3,2-d]pyrimidin-4-yl)-1H-pyrazol-5-amine with Vilsmeier–Haack reagent and subsequent treatment with ammonium carbonate. The structure of the synthesized [...] Read more.

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Graphical abstract

Supplementary material:
Supplementary File 1 (ZIP, 1133 KiB)
Supplementary File 2 (MOL, 3 KiB)
Supplementary File 3 (INCHI, 928 B)
Supplementary File 4 (MOL, 3 KiB)

7 pages, 950 KiB

Open AccessFeature PaperShort Note

3-(4-Bromophenyl)-4-{[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](m-tolyl)methyl}isoxazol-5(2H)-one

by Yuliya E. Ryzhkova, Fedor V. Ryzhkov and Michail N. Elinson

Molbank 2020, 2020(2), M1135; https://doi.org/10.3390/M1135 - 13 May 2020

Viewed by 2483

Abstract

In this communication, the electrochemically induced multicomponent transformation of 3-methylbenzaldehyde, 3-(4-bromophenyl)isoxazol-5(4H)-one and kojic acid in n-PrOH in an undivided cell in the presence of sodium bromide was carefully investigated to give 3-(4-bromophenyl)-4-{[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](m-tolyl)methyl}isoxa- zol-5(2H)-one in good yield. The structure of the new compound was established by means of elemental analysis, mass-, nuclear magnetic resonance and infrared spectroscopy. Furthermore, its structure was determined and confirmed by X-ray analysis. The synthesized compound is a promising compound for different biomedical applications, and, in particular, for the regulation of inflammatory diseases, as shown by docking studies in this research. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Supplementary material:
Supplementary File 1 (MOL, 1 KiB)
Supplementary File 2 (INCHI, 323 B)
Supplementary File 3 (MOL, 1 KiB)
Supplementary File 4 (PDF, 2865 KiB)
Supplementary File 5 (MOL, 1 KiB)
Supplementary File 6 (INCHI, 341 B)
Supplementary File 7 (MOL, 1 KiB)
Supplementary File 8 (MOL, 2 KiB)
Supplementary File 9 (INCHI, 424 B)
Supplementary File 10 (MOL, 2 KiB)
Supplementary File 11 (MOL, 1 KiB)
Supplementary File 12 (INCHI, 461 B)
Supplementary File 13 (MOL, 1 KiB)
Supplementary File 14 (MOL, 2 KiB)
Supplementary File 15 (INCHI, 486 B)
Supplementary File 16 (MOL, 2 KiB)

7 pages, 567 KiB

Open AccessCommunication

Synthesis and Spectral Characterization of 4,7-Dichloro-6-nitroquinazoline

by Thi Ngoc Nguyen, Thi Huong Tran, Nguyet Suong Huyen Dao, Van Giang Nguyen, Dinh Luyen Nguyen, Nguyen Trieu Trinh and Van Hai Nguyen

Molbank 2020, 2020(2), M1134; https://doi.org/10.3390/M1134 - 11 May 2020

Cited by 1 | Viewed by 3241

Abstract

Afatinib is a 4-anilinoquinazoline tyrosine kinase inhibitor (TKI) in the form of a dimaleate salt which is indicated for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC). The most scalable route for the synthesis of this drug was reported in two Boehringer Ingelheim patents, in which the title compound, 4,7-dichloro-6-nitroquinazoline (IV), is an important intermediate. Compound IV is also present in a number of synthetic pathways for various 4,7-disubstituted quinazoline derivatives displaying high therapeutic potential. However, no detailed characterization of this popular compound has been reported, possibly due to its high instability. In this paper, IV was prepared in an overall yield of 56.1% by a 3-step process (condensation, nitration, and chlorination) from 2-amino-4-chlorobenzoic acid (I). The target compound has been for the first time fully characterized by melting point, mass-spectrometry, FT-IR, ¹H-NMR and ¹³C-NMR spectroscopies. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 1075 KiB)
Supplementary File 2 (MOL, 3 KiB)
Supplementary File 3 (INCHI, 838 B)
Supplementary File 4 (MOL, 3 KiB)

6 pages, 819 KiB

Open AccessFeature PaperCommunication

Formation of an Isomeric Mixture of Dienynes Instead of a Diallene

by Susanne M. Petrova and Leiv K. Sydnes

Molbank 2020, 2020(2), M1133; https://doi.org/10.3390/M1133 - 11 May 2020

Cited by 1 | Viewed by 2169

Abstract

Attempts to convert 1,1,2,2,7,7,8,8-octaethoxyocta-3,5-diyne to a symmetric allene by reduction with lithium aluminum hydride failed. Instead reduction accompanied by isomerization occurred and afforded 1,1,2,7,8,8-hexaethoxyocta-2,6-dien-4-yne as a mixture of three isomers in 63% total isolated yield. Full article

(This article belongs to the Collection Molecules from Side Reactions)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 487 KiB)
Supplementary File 2 (MOL, 3 KiB)
Supplementary File 3 (INCHI, 925 B)
Supplementary File 4 (MOL, 3 KiB)

5 pages, 369 KiB

Open AccessShort Note

4’-Methyl-2’-(quinolin-8-ylcarbamoyl)-biphenyl-4-carboxylic Acid Ethyl Ester

by Hamad H. Al Mamari and Anfal Al Hasani

Molbank 2020, 2020(2), M1132; https://doi.org/10.3390/M1132 - 08 May 2020

Cited by 1 | Viewed by 1865

Abstract

In this short note communication, we report the synthesis of a novel amide 4’-methyl-2’-(quinolin-8-ylcarbamoyl)-biphenyl-4-carboxylic acid ethyl ester by the Ru-catalyzed C(sp²)-H bond arylation reaction. The catalytic C-H bond functionalization reaction was employed, amongst other reaction reagents and conditions, [RuCl₂(p-cymene)]₂ as a precatalyst and (p-tol)₃P as a ligand. The arylation product was characterized by various spectroscopic methods (¹H NMR, ¹³C NMR, IR, GC-MS, and IR spectroscopy), and its composition was confirmed by elemental analysis. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 273 KiB)
Supplementary File 2 (MOL, 3 KiB)
Supplementary File 3 (INCHI, 763 B)
Supplementary File 4 (MOL, 3 KiB)

4 pages, 518 KiB

Open AccessShort Note

Methyl 2-(1-methyl-3-oxoisoindolin-1-yl)acetate

by Antonia Di Mola, Antonio Macchia, Laura Palombi and Antonio Massa

Molbank 2020, 2020(2), M1131; https://doi.org/10.3390/M1131 - 08 May 2020

Cited by 1 | Viewed by 2333

Abstract

In this work, we report a facile access to a 3,3-disubstituted isoindolinone by means of Krapcho decarboxylation reaction of the respective substituted dimethyl malonate derivative. Good isolated yields were obtained under mild reaction conditions. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 1092 KiB)
Supplementary File 2 (MOL, 3 KiB)
Supplementary File 4 (MOL, 3 KiB)
Supplementary File 5 (MOL, 2 KiB)
Supplementary File 7 (MOL, 2 KiB)
Supplementary File 8 (MOL, 3 KiB)
Supplementary File 10 (MOL, 3 KiB)
Supplementary File 11 (MOL, 3 KiB)
Supplementary File 13 (MOL, 3 KiB)
Supplementary File 14 (MOL, 3 KiB)
Supplementary File 16 (MOL, 3 KiB)
Supplementary File 17 (MOL, 3 KiB)
Supplementary File 19 (MOL, 3 KiB)

9 pages, 1151 KiB

Open AccessCommunication

Planar-Chiral P and N-bridged Diferrocenes

by Philipp Honegger, Lukas Scheibelberger and Michael Widhalm

Molbank 2020, 2020(2), M1130; https://doi.org/10.3390/M1130 - 04 May 2020

Cited by 1 | Viewed by 2107

Abstract

We describe the synthesis of planar-chiral diferrocene compounds 4, 7 and 12, intended as key precursors for a new family of asymmetric catalyst ligands with less complex structures than their popular equivalents. In contrast to conventional 1,2-disubstituted ferrocenes containing center-chiral and planar-chiral elements, these compounds are purely planar-chiral due to the absence of α-substiuted ethyl groups. The title compounds 4, 7 and 12 were obtained from known precursors in 87%, 59% and 60% yields, respectively. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 557 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 454 B)
Supplementary File 4 (MOL, 2 KiB)

5 pages, 1270 KiB

Open AccessFeature PaperShort Note

2-(Fluoromethyl)-4,7-dimethoxy-1-methyl-1H-benzimidazole

by Patrick Kielty, Pau Farràs, Dennis A. Smith and Fawaz Aldabbagh

Molbank 2020, 2020(2), M1129; https://doi.org/10.3390/M1129 - 01 May 2020

Cited by 1 | Viewed by 3070

Abstract

Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) substitutes the TEMPO free radical with fluorine on 4,7-dimethoxy-1-methyl-2-{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-1H-benzimidazole to give the title compound in a 77% yield. A mechanism is proposed for the formation of this novel methylene fluoride. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 710 KiB)
Supplementary File 2 (MOL, 1 KiB)
Supplementary File 3 (INCHI, 450 B)
Supplementary File 4 (MOL, 1 KiB)
Supplementary File 5 (MOL, 1 KiB)
Supplementary File 6 (INCHI, 450 B)
Supplementary File 7 (MOL, 1 KiB)

6 pages, 841 KiB

Open AccessCommunication

Synthesis of (R) and (S)-3-Chloro-5-(3-methylmorpholino)-4H-1,2,6-thiadiazin-4-ones

by Andreas S. Kalogirou, Christopher R. M. Asquith and Panayiotis A. Koutentis

Molbank 2020, 2020(2), M1128; https://doi.org/10.3390/M1128 - 27 Apr 2020

Cited by 1 | Viewed by 2309

Abstract

Reaction of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one with (R) and (S)-3-methylmorpholines (2 equiv), in THF, at ca. 20 °C gave (R) and (S)-3-chloro-5-(3-methylmorpholino)-4H-1,2,6-thiadiazin-4-ones in 95 and 97% yields, respectively. The new compounds were fully characterized. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 1983 KiB)
Supplementary File 2 (MOL, 1 KiB)
Supplementary File 3 (INCHI, 459 B)
Supplementary File 4 (MOL, 1 KiB)
Supplementary File 5 (MOL, 2 KiB)
Supplementary File 6 (INCHI, 628 B)
Supplementary File 7 (MOL, 2 KiB)

9 pages, 3536 KiB

Open AccessCommunication

Microwave-Assisted Synthesis and Fluorescent Properties of 4-Phenyl-1,8-naphthalimide

by Frank Betancourt, James Helmkay and Hongbin Yan

Molbank 2020, 2020(2), M1127; https://doi.org/10.3390/M1127 - 24 Apr 2020

Cited by 1 | Viewed by 3100

Abstract

4-Phenyl-1,8-naphthalimide was synthesized by imidation of commercially available 4-bromo-1,8-naphthalic anhydride, followed by Suzuki coupling with phenyl boronic acid, both under microwave heating. The microwave-assisted reactions were found to be faster and more efficient than reactions carried out by heating in oil-baths. While this compound was quite fluorescent in solvents such as chloroform, methanol and ethanol, it is virtually non-fluorescent in DMSO; however, upon the addition of water to DMSO solutions of this dye, fluorescence was restored, suggesting a tendency for aggregation-induced emission. The fluorescent properties of 4-phenyl-1,8-naphthalimide were found to be influenced by salt concentrations, likely as a result of hydrophobic effects. While this dye does not show binding to DNA, presence of bovine serum albumin leads to effective fluorescence quenching. Full article

(This article belongs to the Section Organic Synthesis)

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Figure 1

4 pages, 1182 KiB

Open AccessShort Note

3,5-Dithiatricyclo[5.2.1.0^2,6]decan-4-one

by R. Alan Aitken, Neil S. Keddie and Alexandra M. Z. Slawin

Molbank 2020, 2020(2), M1126; https://doi.org/10.3390/M1126 - 24 Apr 2020

Cited by 1 | Viewed by 1890

Abstract

The X-ray structure of the title compound has been determined and the structure shows an exo-configured planar dithiolanone ring. This is in contrast to the few previous dithiolanones to be characterised crystallographically, which are all twisted. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 337 KiB)
Supplementary File 2 (MOL, 7 KiB)
Supplementary File 3 (INCHI, 4 KiB)
Supplementary File 4 (MOL, 7 KiB)
Supplementary File 5 (MOL, 3 KiB)
Supplementary File 6 (INCHI, 2 KiB)
Supplementary File 7 (MOL, 3 KiB)
Supplementary File 8 (CIF, 3425 KiB)

5 pages, 1117 KiB

Open AccessShort Note

Improved Synthesis and Determination of the Biologically Active Diastereomer of YK11

by Yuichiro Kanno, Taichi Kusakabe, Nao Saito, Shoko Kikkawa, Keisuke Takahashi, Isao Azumaya, Kiyomitsu Nemoto and Keisuke Kato

Molbank 2020, 2020(2), M1125; https://doi.org/10.3390/M1125 - 21 Apr 2020

Cited by 4 | Viewed by 3621

Abstract

The palladium catalyzed carbonylation of 1 using the chiral ligand L1 afforded 2 in a highly diastereoselective manner. The stereochemistry of the major diastereomer 2a was determined by X-ray crystallographic analysis. AR luciferase reporter assay studies suggested that 2a was the active constituent [...] Read more.

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Supplementary material:
Supplementary File 1 (MOL, 3 KiB)
Supplementary File 2 (INCHI, 952 B)
Supplementary File 3 (MOL, 3 KiB)
Supplementary File 4 (PDF, 484 KiB)
Supplementary File 5 (ZIP, 493 KiB)

4 pages, 501 KiB

Open AccessShort Note

Dimethyl 2-(1-Methyl-3-oxo-1,3-dihydroisobenzofuran-1-yl)malonate

by Antonia Di Mola, Rosanna Filosa and Antonio Massa

Molbank 2020, 2020(2), M1124; https://doi.org/10.3390/M1124 - 06 Apr 2020

Cited by 1 | Viewed by 2245

Abstract

In this work we report a facile access to a 3,3-disubstituted isobenzofuranone by tandem addition/cyclization reaction to methyl 2-acetylbenzoate in the presence of dimethyl malonate, under basic conditions. Full article

(This article belongs to the Collection Molecules from Catalytic Processes)

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Graphical abstract

Supplementary material:
Supplementary File 1 (ZIP, 1602 KiB)
Supplementary File 2 (MOL, 3 KiB)
Supplementary File 3 (INCHI, 922 B)
Supplementary File 4 (MOL, 3 KiB)
Supplementary File 5 (CIF, 451 KiB)

7 pages, 2065 KiB

Open AccessShort Note

2,6-exo-8,12-exo-10-Butyl-13-oxa-3,5-dithia-10-azatetracyclo[5.5.1.0^2,6.0^8,12]tridecane-9,11-dione

by R. Alan Aitken, Fiona M. Fotherby and Alexandra M. Z. Slawin

Molbank 2020, 2020(2), M1123; https://doi.org/10.3390/M1123 - 02 Apr 2020

Cited by 2 | Viewed by 2642

Abstract

The title compound was obtained in low yield and spectroscopically characterised. Its X-ray structure was compared with the X-ray structures of other crystallographically-characterised 2-unsubstituted 1,3-dithiolanes. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

Supplementary material:
Supplementary File 1 (PDF, 518 KiB)
Supplementary File 2 (MOL, 6 KiB)
Supplementary File 3 (INCHI, 2 KiB)
Supplementary File 4 (MOL, 6 KiB)
Supplementary File 5 (MOL, 6 KiB)
Supplementary File 6 (INCHI, 2 KiB)
Supplementary File 7 (MOL, 6 KiB)
Supplementary File 8 (MOL, 4 KiB)
Supplementary File 9 (INCHI, 1 KiB)
Supplementary File 10 (MOL, 4 KiB)
Supplementary File 11 (MOL, 3 KiB)
Supplementary File 12 (INCHI, 1003 B)
Supplementary File 13 (MOL, 3 KiB)

8 pages, 1272 KiB

Open AccessCommunication

Unexpected Seven-Membered Ring Formation for Muraymycin-Type Nucleoside-Peptide Antibiotics

by Kristin Leyerer, Stefan Koppermann and Christian Ducho

Molbank 2020, 2020(2), M1122; https://doi.org/10.3390/M1122 - 26 Mar 2020

Cited by 1 | Viewed by 2290

Abstract

Naturally occurring nucleoside-peptide antibiotics such as muraymycins or caprazamycins are of major interest for the development of novel antibacterial agents. However, the synthesis of new analogues of these natural products for structure–activity relationship (SAR) studies is challenging. In our synthetic efforts towards a muraymycin-derived nucleoside building block suitable for attachment to a solid support, we came across an interesting side product. This compound resulted from an undesired Fmoc deprotection with subsequent cyclization, thus furnishing a remarkable caprazamycin-like seven-membered diazepanone ring. Full article

(This article belongs to the Collection Molecules from Side Reactions)

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