Synlett 2004(4): 703-707  
DOI: 10.1055/s-2004-817788
LETTER
© Georg Thieme Verlag Stuttgart · New York

New Reactivity of Nitropyrimidinone: Ring Transformation and N-C Transfer Reactions

Nagatoshi Nishiwaki*, Kazuo Matsushima, Miki Chatani, Mina Tamura, Masahiro Ariga*
Department of Chemistry, Osaka Kyoiku University, Asahigaoka 4-698-1, Kashiwara, Osaka 582-8582, Japan
Fax: +81(729)783399; e-Mail: ariga@cc.osaka-kyoiku.ac.jp;
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Publication History

Received 9 December 2003
Publication Date:
17 February 2004 (online)

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Abstract

Nitropyrimidinone 1 revealed new reactivity upon treatment with active methylene compounds 2 under basic conditions. The N1-C2-C3-C4 moiety of 1 combined with two carbon units of 2 affording polyfunctionalized pyridones 4, which was hitherto unknown ring transformation. On the other hand, the N1-C2 moiety of 1 was transferred to the methylene group of 2 giving functionalized enamines 3. It was also possible to modify the amino group in 3a by reactions with primary amines. Enamines 3 reacted with hydrazines, and leading to functionalized pyrazoles 7 quantitatively. The ratios of regioisomeric pyrazoles 7/8 were moderately controlled by use of sterically hindered enamines 3h, 3k and 3l. Furthermore, enamine 3a was readily converted to 1,4-diazepines 9 having a functional group at the 6-position.