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Synthesis and molecular structure of 6-aryl-3-ethoxycarbonyl-4-hydroxypyridazines

Authors:	Z. G. Aliev N. G. Vyaznikova V. V. Zalesov S. S. Kataev Yu. S. Andreichikov L. O. Atovmyan

Affiliation:	(1) Institute of Chemical Physics in Chernogolovka, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation;(2) Pharmaceutical Academy, 48 ul. Lenina, 614000 Perm, Russian Federation;(3) Perm' State University, 15 ul. Bukireva, 614600 Perm', Russian Federation;(4) Institute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences, 13 ul. Lenina, 614600 Perm', Russian Federation

Abstract:	EthylZ-5-aryl-2-diazo-5-hydroxy-3-oxopent-4-enoates interact with triphenylphosphine to give 6-aryl-3-ethoxycarbonyl-4-hydroxypyridazines (Ar=Ph, 4-MeC₆H₄, 4-ClC₆H₄). Quantum-chemical calculations (MNDO) were performed to estimate the tautomeric equilibrium in the latter using a 6-phenyl-substituted derivative as an example. Acetylation of the 4-hydroxypyridazines led to 4-acetoxy-6-aryl-3-ethoxycarbonylpyridazines. The structure of the latter was confirmed by an X-ray diffraction analysis of 4-acetoxy-3-ethoxycarbonyl-6-(p-tolyl)pyridazine. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2260–2263, December, 1997.

Keywords:	diazo compounds substituted pyridazines acylation molecular and crystal structure
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