Regioselective Aryl Radical Cyclization: Access to Pyrimidine-Annelated Spiro Heterocycles Through 5-exo Ring Closure

K. C. Majumdar; P. P. Mukhopadhyay

doi:10.1055/s-2004-829133

PAPER

Regioselective Aryl Radical Cyclization: Access to Pyrimidine-Annelated Spiro Heterocycles Through 5-exo Ring Closure

K. C. Majumdar*, P. P. Mukhopadhyay
Department of Chemistry, University of Kalyani, Kalyani 741 235, West Bengal, India
Fax: +91(33)25828282; e-Mail: kcm@klyuniv.ernet.in;

Abstract

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Abstract

Aryl radical cyclization of a range of 6-(2′-bromophenoxymethyl)-1,3-dimethyluracils 4a-g was carried out with tributyltin chloride and sodium cyanoborohydride in the presence of AIBN for four hours to give exclusively the ‘5-exo’ cyclization products, 1,3-dimethylspiro[pyrimidine-6,3′-2′,3′-tetrahydrobenzofuran]-2,4-diones 5a-g in 92-95% yield. The starting materials were in turn prepared in 90-92% yield by refluxing 6-chloro methyl-1,3-dimethyl uracil with various 2-bromophenols or 2-bromonaphthol in acetone in the presence of anhydrous potassium carbonate for eight hours.

Key words

heterocyclic compounds - spiro heterocycles - organotin reagent - 6-chloromethyl-1,3-dimethyl uracil - radical cyclization - 5-exo-trig

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