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The synthesis of pyridazino[4,5‐d] pyridazines, pyrazino [2,3‐d] pyridazines and a pyrimido [4,5‐d] pyridazine

 

作者: Lorraine DiStefano,   Raymond N. Castle,  

 

期刊: Journal of Heterocyclic Chemistry  (WILEY Available online 1968)
卷期: Volume 5, issue 1  

页码: 53-59

 

ISSN:0022-152X

 

年代: 1968

 

DOI:10.1002/jhet.5570050110

 

出版商: Wiley‐Blackwell

 

数据来源: WILEY

 

摘要:

AbstractThe synthetic chemistry of the relatively unknown pyridazino [4,5‐d]pyridazine ring system has been extended. 1,4‐Diaminopyridazino [4,5‐d]pyridazine (VIII) has been prepared by two routes, the most interesting of these being the one‐step conversion of 4,5‐dicyanopyridazine into VIII with hydrazine. Upon nitration VIII gave only the mononitramine (X). Attempts to prepare 1,4‐dichloropyridazino [4,5‐d]pyridazine gave only 4‐chloro‐2H‐pyridazino [4,5‐d]pyridazin‐1‐one (XII). Pyrimido [4,5‐d]pyridazine‐1,3‐dione (XIV) was prepared from pyridazine‐4,5‐dicarboxamide (IV). The hydrolysis of 5,8‐dichloropyrazino [2,3‐d]pyridazine (XV) gave 5‐chloropyrazino [2,3‐d]pyridazin‐8‐one (XVII) and likewise the ammonolysis of XV gave 5‐amino‐8‐chloropyrazino [2,3‐d]pyridazine (XX). As expected the hydrolysis of 5,8‐dibromo‐pyrazino [2,3‐d]pyridazine (XXI) gave 5‐bromopyrazino [2,3‐d]pyridazin‐8‐one (XXII). Attempted catalytic dechlorination of 5‐chloropyrazino [2,3‐d]pyridazin

 

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