Chlorination of ethyl(quinoxalin-2(1H)one)-3-carboxylate 1 gave ethyl (2-chloroquinoxaline)-3-carboxylate 2;thionation of 1 by P2S5 or 2 by thiourea yielded the same product 3. Reaction of chloro compound 2 or thiocompound 3 with hydrazine hydrate gave pyrazolylquinoxaline 4. The reaction of ester 1 with thiourea or hydrazine hydrate afforded pyrimido quinoxaline 5 or carbohydrazide 6; the reaction of 6 with carbon disulfide in basic medium followed by alkylation afforded oxadiazoloquinoxaline derivatives 7, 8a,b. Carboazide 9 was produced by reaction of 5 with nitrous acid. Compound 9 on heating in an inert solvent, with or without amines, in alcohols or hydrolysis in H2O undergoes Curtius rearrangments to yield 10-13. Reaction of 13 with thiosemicarbazide gave triazoloquinoxaline 14 which on reaction with alkylhalides or hydrazine hydrate yielded 15a-c while hydrolysis of 13 gave 3-aminoquinoxalinone 16 which was used as an intermediate to produce 17-20.

中文翻译：

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喹喔啉卡巴肼的合成及部分反应

(喹喔啉-2(1H)one)-3-甲酸乙酯 1 氯化得到 (2-氯喹喔啉)-3-甲酸乙酯 2；P2S5 使 1 或硫脲使 2 硫化得到相同的产物 3。氯化合物 2 的反应或硫代化合物3与水合肼得到吡唑基喹喔啉4。酯1与硫脲或水合肼反应得到嘧啶基喹喔啉5或碳酰肼6；6 在碱性介质中与二硫化碳反应，然后烷基化，得到恶二唑并喹喔啉衍生物 7、8a、b。Carboazide 9 由 5 与亚硝酸反应生成。化合物 9 在惰性溶剂中加热，有或没有胺，在醇中或在 H2O 中水解，会发生 Curtius 重排，得到 10-13。