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KMID : 1059519900340050469
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Journal of the Korean Chemical Society
1990 Volume.34 No. 5 p.469 ~ p.475
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A Selective Synthesis of Isoxazolo[2,3-a]quinoxalines and Pyrrolo[1,2-a]quinoxalines by 1,3-Dipolar Cycloaddition Reaction
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Kim Ho-Sik
Nam Soon-Hwa
Yoshihisa Kurasawa
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Abstract
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The reaction of 2,6-dichloroquinoxaline (13) with m-chloroperbenzoic acid gave 2,6-dichloroquinoxaline 4-oxide (14), whose reaction with pyrrolidine or indoline provided 2-substituted 6-chloroquinoxaline 4-oxides (15). The isoxazolo[2,3-a]quinoxalines (16) and pyrrolo[1,2-a]quinoxalines (17) were selectively synthesized from the 2-substituted 6-chloroquinoxaline 4-oxides (15) and dimethyl acetylenedicarboxylate. Moreover, the pyrrolo[1,2-a]quinoxalines (17) were found to be produced by the ring transformation of the isoxazolo[2,3-a]quinoxalines (16).
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