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A convenient synthesis of 2-amino-4H-1,3,4-oxadiazino[5,6-b]-quinoxaline derivatives

✍ Scribed by Ho Sik Kim; Tong Eun Kim; Seong Uk Lee; Dong Il Kim; Sung Wook Han; Yoshihisa Okamoto; Takako Mitomi; Yoshihisa Kurasawa

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
380 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of 6‐chloro‐2‐(1‐methylhydrazino)quinoxaline 4‐oxide 5 with a 2‐fold molar amount of ethyl chloroglyoxalate gave ethyl 8‐chloro‐4‐methyl‐4__H__‐1,3,4‐oxadiazino[5,6‐b]quinoxaline‐2‐carboxylate 6, whose reaction with hydrazine hydrate afforded the C~2~‐hydrazinocarbonyl derivative 7. The reaction of compound 7 with nitrous acid provided the C~2~‐acylazide derivative 8, which was converted into the C~2~‐amino 9, C~2~‐carbamate 11a‐c, 12a,b, and C~2~‐ureido 13a‐c, 14 derivatives. The mass spectral fragmentation patterns were examined for compounds 10–14, wherein the molecular ion peak did not appear in the mass spectra of compounds 10c, 11a‐c, 12a,b, 13c, and 14.

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