Rapid synthesis of azepinoindole derivatives from tryptamine sulfonamides and bromoallyl sulfones via an acid-mediated cyclization and rearrangement-Reference-Cited by-同舟云学术

Rapid synthesis of azepinoindole derivatives from tryptamine sulfonamides and bromoallyl sulfones via an acid-mediated cyclization and rearrangement

Published:2021 Issue:5 Volume:57 Page:635-638
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Gurram Ravikumar¹²³⁴,Nanubolu Jagadeesh Babu⁵²³⁴⁶,Menon Rajeev S.⁷⁸⁹⁴^ORCID

Affiliation:

1. Department of Organic Synthesis & Process Chemistry

2. CSIR-Indian Institute of Chemical Technology

3. Tarnaka

4. India

5. Analytical Department

6. Academy of Scientific and Innovative Research (AcSIR)

7. Department of Chemistry

8. Central University of Haryana

9. Mahendergarh

Abstract

The azepinoindole framework present in natural alkaloids such as subincanadine F, ibogaine and catharanthine was formed in a novel acid-promoted cyclization–rearrangement of tryptamine-derived N-sulfonyl enamines.

Funder

Science and Engineering Research Board

Council of Scientific and Industrial Research, India

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2021/CC/D0CC06991D

Reference23 articles.

1. Subincanadines A−C, Novel Quaternary Indole Alkaloids from Aspidosperma subincanum

2. Two New Indole Alkaloids from Aspidosperma subincanum and Geissospermum vellosii

3. Progress in total synthesis of subincanadine alkaloids and their congeners

4. Total Synthesis of Indole Alkaloid (±)-Subincanadine F via SmI2-Mediated Ring Opening and Bridge-Forming Mannich Reaction

5. Protecting-Group-Free Total Synthesis of (±)-Subincanadine F

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