Novel Method of Synthesizing Various Five Membered Heterocycles from an Aryl Tribromomethyl Group

Abstract

Synthesis of five membered heterocycles from an aryl tribromomethyl functional group is discussed. Exposing a tribromomethyl group to subsequent nucleophilic attacks by a 1,2-di-nucleophilic species promotes the cyclization of five membered heterocycles. Such heterocycles as oxadiazoles, thiadiazole, benzimidazole, benzothioazole, and benzoxazole were synthesized in moderate to good yields.

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GRAPHICAL ABSTRACT

Keywords:

• Cyclization
• heterocycles
• tribromomethyl

Notes

^a 3 eq of base.

^b Parentheses indicate LCMS conversion of 7 with respect to intensity of 6a and b.

^c Isolated yield of 7.

^d Recovered 34% of 5.