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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 34, Number 5
JKCSEZ 34(5)
October 20, 1990 

A Selective Synthesis of Isoxazolo[2,3-a]quinoxalines and Pyrrolo[1,2-a]quinoxalines by 1,3-Dipolar Cycloaddition Reaction

1,3-쌍극성 고리화 첨가반응에 의한 Isoxazolo[2,3-a]quinoxaline류와 Pyrrolo[1,2-a]quinoxaline류의 선택적인 합성
Ho Sik Kim, Soon Hwa Nam, Yoshihisa Kurasawa

김호식, 남순화, 창택가구
2,6-dichloroquinoxaline (13)과 m-chloroperbenzoic acid를 반응시켜 2,6-dichloroquinoxaline 4-oxide (14)를 합성하고, 이것과 pyrrolidine 혹은 indoline을 반응시켜 2-substituted 6-chloroquinoxaline 4-oxide류(15)를 합성하였다. 그리고 이들과 dimethyl acetylenedicarboxylate를 반응시키니 isoxazolo[2,3-a]quinoxaline류(16)와 pyrrolo[1,2-a]quinoxaline류 (17)가 선택적으로 합성되었다. 더욱이 pyrrolo[1,2-a]quinoxaline류 (17)는 isoxazolo[2,3-a]quinoxaline류 (16)의 고리변환에 의하여 생성된다는 것을 알았다.

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).

469 - 475
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