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Synthesis 2008(21): 3497-3503  
DOI: 10.1055/s-0028-1083183
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 5-Amino-4-(2-azacycloalkylidene)-2-phenyl-2,4-dihydro-3H-pyrazol-3-ones

Konstantin G. Nazarenko*a, Sergey I. Bovab, Vitaliy Polovinkoc, Andrey A. Tolmachevc
a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska st., Kyiv 02094, Ukraine
Fax: +380(44)5732643; e-Mail: nazarenko@ioch.kiev.ua;
b Chernigiv State Technological University, 95 Shevchenko st., Chernigiv 14027, Ukraine
c Research and Development Center for Chemistry and Biology, National Taras Shevchenko University, 62 Volodymyrska st., Kyiv 01033, Ukraine
Further Information

Publication History

Received 24 June 2008
Publication Date:
16 October 2008 (online)

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Abstract

The reaction 5-amino-2-phenyl-3,4-dihydro-3H-pyrazol-3-one with activated lactams (lactim ethers, lactam acetals, and methylthioalkylidene iminium salts) was investigated. It occurs on the active methylene group of 5-amino-2-phenyl-3,4-dihydro-3H-pyrazol-3-one to furnish cyclic enamines, 5-amino-4-(2-azacycloalkylidene)-2-phenyl-2,4-dihydro-3H-pyrazol-3-ones and 5-amino-4-(1-methyl-2-azacycloalkylidene)-2-phenyl-2,4-dihydro-3H-pyrazol-3-ones.

Key words

lactams - pyrazolone - cyclic enamine - ring opening - heterocycles

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