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Cyclization Reactions in Organic Synthesis: Recent Developments

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 30 June 2024 | Viewed by 1712

Special Issue Editors


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Guest Editor
University of Coimbra, Coimbra Chemistry Centre-Institute of Molecular Sciences (CQC-IMS), Department of Chemistry, Coimbra, Portugal
Interests: organic synthesis; heterocyclic chemistry; cycloaddition reactions; allenes; 2H-azirines; mecanochemistry

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Guest Editor
Department of Chemistry, Coimbra Chemistry Centre–Institute of Molecular Sciences, University of Coimbra, 3004-535 Coimbra, Portugal
Interests: organic synthesis; heterocyclic chemistry; medicinal chemistry; oxygen heterocycles; allenes; cycloaddition reactions; annulation reactions; flash vacuum pyrolysis
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Special Issue Information

Dear Colleagues,

Cyclization reactions are a powerful tool in organic synthesis for the construction of cyclic compounds, which present a wide variety of applications in several areas, such as drug discovery, agrochemicals, and materials science.

One of the most significant advantages of these transformations is the ability to generate molecular complexity with high stereochemical control, a crucial feature in the synthesis of natural products and in the pharmaceutical industry. Additionally, these processes enable the synthesis of complex structures with specific ring sizes and shapes, including strained rings, which are difficult to obtain otherwise. Moreover, they often require fewer steps and reagents compared to the classical synthetic methods, resulting in less waste generation and a reduction in the environmental impact, in line with the principles of green chemistry.

In recent decades, cyclization reactions have become increasingly important in organic synthesis and have contributed to the development of novel bioactive compounds, agrochemicals, and polymers, as well as new synthetic routes to natural products.

This Special Issue, “Cyclization Reactions in Organic Synthesis: Recent Developments”, aims to gather the most recent advances on this topic. Full papers, communications, and reviews are all welcome for submission.

Dr. Ana L. Cardoso
Dr. Maria Isabel L. Soares
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • cyclization reactions
  • radical cyclization
  • cascade reaction
  • asymmetric cyclization
  • cycloaddition reactions
  • carbocyclic compounds
  • heterocyclic compounds
  • bioactive compounds

Published Papers (2 papers)

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Research

20 pages, 2678 KiB  
Article
Nickel(II)-Catalyzed Formal [3+2] Cycloadditions between Indoles and Donor–Acceptor Cyclopropanes
by Víctor Quezada, Mariña Castroagudín, Felipe Verdugo, Sergio Ortiz, Guillermo Zaragoza, Fabiane M. Nachtigall, Francisco A. A. Reis, Alejandro Castro-Alvarez, Leonardo S. Santos and Ronald Nelson
Molecules 2024, 29(7), 1604; https://doi.org/10.3390/molecules29071604 - 03 Apr 2024
Viewed by 672
Abstract
This article describes the development of a nickel-catalyzed regio- and diastereoselective formal [3+2] cycloaddition between N-substituted indoles and donor–acceptor cyclopropanes to synthesize cyclopenta[b]indoles. Optimized reaction conditions provide the desired nitrogen-containing cycloadducts in up to 93% yield and dr 8.6:1 with [...] Read more.
This article describes the development of a nickel-catalyzed regio- and diastereoselective formal [3+2] cycloaddition between N-substituted indoles and donor–acceptor cyclopropanes to synthesize cyclopenta[b]indoles. Optimized reaction conditions provide the desired nitrogen-containing cycloadducts in up to 93% yield and dr 8.6:1 with complete regioselectivity. The substrate scope showed high tolerance to various substituted indoles and cyclopropanes, resulting in the synthesis of six new cyclopenta[b]indoles and the isolation of five derivatives previously reported in the literature. In addition, a mechanistic proposal for the reaction was studied through online reaction monitoring by ESI-MS, allowing for the identification of the reactive intermediates in the Ni(II) catalyzed process. X-ray crystallography confirmed the structure and relative endo stereochemistry of the products. This method enables the fast and efficient construction of fused indolines from readily accessible starting materials. Full article
(This article belongs to the Special Issue Cyclization Reactions in Organic Synthesis: Recent Developments)
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16 pages, 2928 KiB  
Article
Persulfate-Promoted Carbamoylation/Cyclization of Alkenes: Synthesis of Amide-Containing Quinazolinones
by Jia-Jun Tang, Meng-Yang Zhao, Ying-Jun Lin, Li-Hua Yang and Long-Yong Xie
Molecules 2024, 29(5), 997; https://doi.org/10.3390/molecules29050997 - 25 Feb 2024
Viewed by 532
Abstract
The incorporation of amide groups into biologically active molecules has been proven to be an efficient strategy for drug design and discovery. In this study, we present a simple and practical method for the synthesis of amide-containing quinazolin-4(3H)-ones under transition-metal-free conditions. [...] Read more.
The incorporation of amide groups into biologically active molecules has been proven to be an efficient strategy for drug design and discovery. In this study, we present a simple and practical method for the synthesis of amide-containing quinazolin-4(3H)-ones under transition-metal-free conditions. This is achieved through a carbamoyl-radical-triggered cascade cyclization of N3-alkenyl-tethered quinazolinones. Notably, the carbamoyl radical is generated in situ from the oxidative decarboxylative process of oxamic acids in the presence of (NH4)2S2O8. Full article
(This article belongs to the Special Issue Cyclization Reactions in Organic Synthesis: Recent Developments)
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