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Dearomatization Strategies in the Synthesis of Complex Carbo- and Heterocyclic Systems

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

Deadline for manuscript submissions: closed (31 March 2024) | Viewed by 937

Special Issue Editors


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Guest Editor
N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, 119991 Moscow, Russia
Interests: nitro compounds; heterocyclic chemistry; cycloadditions; pyridines; azoles; synthetic methods; bologically active compounds
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian
Interests: organic snthesis; heterocyclic compounds; nitro compounds; nitrogen heterocycles; biologically active compounds; dearomatization; cycloaddition reactions
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian
Interests: nitrogen heterocycles; heterocyclic chemistry; organic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Dearomatization has become a challenging research topic in modern synthetic organic chemistry as well as one of the most powerful methods for the conversion of simple aromatic substrates into diverse structurally complex systems. This approach delivers more concise synthetic routes to target molecules due to a considerable increase in complexity at the dearomatization step. This appears very useful, in particular, for the total synthesis of natural products as well as pharmaceutically oriented hybrid compounds.

In this Special Issue, original research papers and high-quality reviews on the application of the dearomatization approach are welcome. This Special Issue will focus on research advances and developments in dearomatization strategies toward various condensed, spiroconjugated carbo- and heterocyclic skeletons made directly from simple and readily available (hetero)aromatics.

Dr. Alexey M. Starosotnikov
Dr. Maxim A. Bastrakov
Dr. Igor L. Dalinger
Guest Editors

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Keywords

  • organic synthesis
  • dearomatization reactions
  • fused carbo- and heterocycles
  • dearomative spirocyclizations
  • [4+2]-cycloaddition
  • 1,3-dipolar cycloaddition
  • (hetero)arenes
  • synthetic methods
  • transition metal catalysis

Published Papers (1 paper)

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Research

18 pages, 1714 KiB  
Article
Synthesis of Benzofuro[3,2-b]indol-3-one Derivatives via Dearomative (3 + 2) Cycloaddition of 2-Nitrobenzofurans and para-Quinamines
by Wei-Cheng Yuan, Hai-Ying Zeng, Yan-Ping Zhang, Jian-Qiang Zhao, Yong You, Jun-Qing Yin, Ming-Qiang Zhou and Zhen-Hua Wang
Molecules 2024, 29(5), 1163; https://doi.org/10.3390/molecules29051163 - 05 Mar 2024
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Abstract
An efficient dearomative (3 + 2) cycloaddition of para-quinamines and 2-nitrobenzofurans has been developed. This reaction proceeds smoothly under mild conditions and affords a series of benzofuro[3,2-b]indol-3-one derivatives in good to excellent yields (up to 98%) with perfect diastereoselectivities (all [...] Read more.
An efficient dearomative (3 + 2) cycloaddition of para-quinamines and 2-nitrobenzofurans has been developed. This reaction proceeds smoothly under mild conditions and affords a series of benzofuro[3,2-b]indol-3-one derivatives in good to excellent yields (up to 98%) with perfect diastereoselectivities (all cases > 20:1 dr). The scale-up synthesis and versatile derivatizations demonstrate the potential synthetic application of the protocol. A plausible reaction mechanism is also proposed to account for the observed reaction process. This work represents the first instance of the N-triggered dearomative (3 + 2) cycloaddition of 2-nitrobenzofurans. Full article
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