An efficient synthesis of spiro- β-lactams having sulfenyl, sulfinyl and sulfonyl moiety

An efficient and a facile route to spiro- β -lactams is described. 3-allyl-3-methylthio- β -lactams, which are synthesized through a Lewis acid mediated C-3 alkylation of the trans -3-chloro-3-methylthio- β -lactams, undergo a facile intrasulfenyl cyclization reaction in the presence of halogens lik...

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Bibliographic Details
Published in:Journal of chemical sciences (Bangalore, India) India), 2015-11, Vol.127 (11), p.1957-1966
Main Authors: RESHMA, ARORA, RENU, HUNDAL, GEETA, BHALLA, AMAN, BARI, S S
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Summary:An efficient and a facile route to spiro- β -lactams is described. 3-allyl-3-methylthio- β -lactams, which are synthesized through a Lewis acid mediated C-3 alkylation of the trans -3-chloro-3-methylthio- β -lactams, undergo a facile intrasulfenyl cyclization reaction in the presence of halogens like bromine and iodine to give spiro β -lactams in good yield. These halospiro- β -lactams are then subjected to dehalogenation reaction using Raney-nickel. The resulting spiro- β -lactams are further transformed into their sulfinyl and sulfonyl derivatives by using m -chloroperbenzoic acid as an oxidant. Graphical Abstract A facile synthesis of novel sulfinyl and sulfonyl spiro-β-lactams through intramolecular cyclization of cis -3-allyl-3-methylthio-β-lactams is described.
ISSN:0974-3626
0973-7103
DOI:10.1007/s12039-015-0956-1