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2005
Pyridazine derivatives
R 0500
Purines, Pyrimidines, and Related Fused Systems. Part 21. Oxidative Amination
3-Chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione. — Oxida02- 151 of
tive amination of the title compound (I) with potassium amide and primary amines provides the corresponding previously unknown vic-chlorohetarylamines (III) and (VI),
resp., as the major products. Similar reaction with piperidine occurs exclusively as aminodehalogenation furnishing the substitution product (XII). Reactions with acyclic secondary amines are accompanied by formation of a pyrrole ring [→(XIV)]. The
vic-chlorohetarylamines (III) smoothly undergo Sonogashira cross-coupling with terminal alkynes furnishing pyrrolopyrimidopyridazine derivatives such as (VI). —
(GORYUNENKO, V. V.; GULEVSKAYA*, A. V.; POZHARSKII, A. F.; Russ.
Chem. Bull. 53 (2004) 4, 846-852; Rostov State Univ., Rostov-on-Don 344090,
Russia; Eng.) — D. Singer
2005
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