TY - JOUR T1 - First iodocyclization reaction of allene-thioureas: an efficient approach to bicyclic beta-lactams JF - Tetrahedron Letters Y1 - 2014 A1 - Garud, Dinesh R. A1 - Jadhav, Amol R. A1 - Lahore, Santosh V. A1 - Kahar, Nilesh M. A1 - Joshi, Rohini R. A1 - Joshi, Ramesh A. A1 - Koketsu, Mamoru KW - Allene KW - beta-Lactams KW - Iodocyclization KW - Regioselective KW - thiourea AB -

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.

PB - PERGAMON-ELSEVIER SCIENCE LTD CY - THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND VL - 55 IS - 43 U3 - Foreign U4 - 2.68 ER -