Authors: Majumdar, K C.; Debnath, P; Pal, A K.; Chattopadhyay, S K.; Biswas, A

Source: Canadian Journal of Chemistry, Volume 85, Number 6, June 2007 , pp. 445-452(8)

Publisher: NRC Research Press

Abstract:

Regiochemical study of ⁿBu₃SnH-AIBN-mediated aryl-radical cyclization of different 3-(2-bromophenyl sul fenylmethyl)coumarins, 3-(2-bromophenylsulfonyl-methyl)coumarins, and 6-[(2-bromophenoxy)methyl]-4-methoxypyran-2-ones have been investigated with the formation of different [6,6]-fused and spirocylic heterocycles. The sulfides and ethers were prepared from 3-chloromethyl coumarin and 6-(bromomethyl)-4-methoxy pyran-2-one with different 2-bromothiophenol and 2-bromophenols under classical alkylation condition. The corresponding sulfones were prepared by oxidation of the sulfides with m-CPBA.Key words: aryl-radical cyclization, coumarin and pyrone derivatives, 5-exo-trig, 5-endo-trig, ⁿBu₃SnH, sulfur heterocycles.

On a effectué des réactions de cyclisation radicalaires aryliques, catalysées par le Bu₃SnH-AIBN, de diverses 3-(2-bromophénylsulfénylméthyl)coumarines, de 3-(2-bromophénylsulfonylméthyl)coumarines et de 6-[(2-bromop hénoxy)méthyl]-4-méthoxypyran-2-ones et on a étudié leur régiochimie par rapport à la formation d'hétérocycles divers spirocycliques ou à fusion [6,6]. On a préparé les sulfures et les éthers de la 3-chlorométhylcoumarine et de la 6-(6-bromométhyl)-4-méthoxypyran-2-one à l'aide de divers 2-bromothiophénols et de 2-bromophénols, dans des conditions d'alkylation classique. Les sulfones correspondantes ont été préparées par oxydation des sulfures à l'aide d'acide m-chloroperbenzoïque.Mots-clés : cyclisation radicalaire arylique, dérivés de la coumarine et des pyrones, 5-exo-trig, 6-endo-trig, Bu₃SnH, hétérocycles sulfurés.[Traduit par la Rédaction]

Document Type: Research article

Publication date: 2007-06-01

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• In this Subject: Chemistry (General) ,  Inorganic Chemistry ,  Organic Chemistry
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