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Synthesis of carbocyclic and heterocyclic fused quinolines by cascade radical annulations of unsaturated N-aryl thiocarbamates, thioamides, and thioureas

Du, W and Curran, DP (2003) Synthesis of carbocyclic and heterocyclic fused quinolines by cascade radical annulations of unsaturated N-aryl thiocarbamates, thioamides, and thioureas. Organic Letters, 5 (10). 1765 - 1768. ISSN 1523-7060

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Abstract

(Matrix presented) Tandem radical cyclizations of suitably substituted N-aryl thiocarbamates, thioamides, and thioureas are induced by exposure to tris(trimethylsilyl)-silane (TTMSH) and UV light and provide furoquinolines, isofuroquinolines, cyclopentaquinolines, indoloquinolines, and related ring systems. The intermediacy of an α-thioalkylamino radical, which is the synthetic equivalent of an imidoyl radical, is invoked.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Du, W
Curran, DPcurran@pitt.eduCURRAN
Date: 15 May 2003
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 5
Number: 10
Page Range: 1765 - 1768
DOI or Unique Handle: 10.1021/ol0344319
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Cyclization; Indicators and Reagents; Quinolines--chemical synthesis; Thioamides--chemistry; Thiocarbamates--chemistry; Thiourea--chemistry; Ultraviolet Rays
PubMed ID: 12735772
Date Deposited: 06 Feb 2014 23:58
Last Modified: 29 Jan 2019 15:55
URI: http://d-scholarship.pitt.edu/id/eprint/20452

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