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:	Creators Email Pitt Username ORCID Du, W Curran, DP curran@pitt.edu CURRAN
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-dev.library.pitt.edu/id/eprint/20452

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