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Some aspects of the chemistry of pyrimido[1,2‐ B ]pyridazinones
Author(s) -
Mátyus Péter,
Szilágyi Géza,
Kasztreiner Endre,
Rabloczky György,
Sohár Pál
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250552
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , medicinal chemistry , organic chemistry , stereochemistry , cycloaddition , catalysis
On reacting the 3‐aminopyridazines 1a,d,e with dimethyl acetylenedicarboxylate (DMAD), the pyrimido[1,2‐ b ]pyridazin‐2‐(2 H )‐ones 2e‐g , whereas starting from 1f , the 4(4 H )‐ones 5a and 3b,d were prepared. In the 2(2 H )‐one series, the reactions of 2b with various amino compounds resulted in various types of products. The reaction of N ‐methylaminopyridazines 1g,h with DMAD led to the endo‐N ‐substituted derivatives 8a,b , whereas 1h with diethyl ethoxymethylenemalonate (DEM) gave the exo‐N ‐substituted compound 1k. The constitution of the compounds was proved by spectroscopic and chemical evidences.