First iodocyclization reaction of allene-thioureas: an efficient approach to bicyclic beta-lactams

TitleFirst iodocyclization reaction of allene-thioureas: an efficient approach to bicyclic beta-lactams
Publication TypeJournal Article
Year of Publication2014
AuthorsGarud, DR, Jadhav, AR, Lahore, SV, Kahar, NM, Joshi, RR, Joshi, RA, Koketsu, M
JournalTetrahedron Letters
Volume55
Issue43
Pagination5998-6000
Date PublishedOCT
ISSN0040-4039
KeywordsAllene, beta-Lactams, Iodocyclization, Regioselective, thiourea
Abstract

The regioselective iodocyclization reaction of allene-thioureas is described, for the first time, for the synthesis of bicyclic beta-lactams. The substitution at the allenyl part heavily influenced the iodocyclization reaction. The iodocyclization reaction of the unsubstituted allene-thioureas afforded six-membered 3-thia-1-dethiacephems whereas, the substituted allene-thiourea afforded seven-membered thiazepines along with five-membered isopenams. (C) 2014 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2014.09.004
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.68
Divison category: 
Organic Chemistry