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

Konstantin G. Nazarenko; Sergey I. Bova; Vitaliy Polovinko; Andrey A. Tolmachev

doi:10.1055/s-0028-1083183

PAPER

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

Konstantin G. Nazarenko*^a, Sergey I. Bova^b, Vitaliy Polovinko^c, Andrey A. Tolmachev^c
^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

Abstract

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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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References

<A NAME="RP07008SS-1">1</A> Patzel M. Liebscher U. Synthesis 1995, 879

<A NAME="RP07008SS-2A">2a</A> Liebscher U. Patzel M. Bechstein U. Synthesis 1989, 968

<A NAME="RP07008SS-2B">2b</A> Radics U. Liebscher U. Patzel M. Synthesis 1992, 673

<A NAME="RP07008SS-3">3</A> Patzel M. Liebscher U. J. Org. Chem. 1992, 57: 1831

<A NAME="RP07008SS-4">4</A> Patzel M. Liebscher U. Arch. Pharm. (Weinheim, Ger.) 1991, 324: 963

<A NAME="RP07008SS-5A">5a</A> Liebscher U. Patzel M. Kelboro YF. Synthesis 1989, 672

<A NAME="RP07008SS-5B">5b</A> Liebscher U. Patzel M. Kelboro YF. Synthesis 1989, 968

<A NAME="RP07008SS-6">6</A> Patzel M. Liebscher U. Andreae S. Schmitz E. Synthesis 1990, 1071

<A NAME="RP07008SS-7A">7a</A> Bohrisch J. Patzel M. Liebscher U. Maas G. Synthesis 1993, 521

<A NAME="RP07008SS-7B">7b</A> Karanik M. Patzel M. Liebscher U. Synthesis 2003, 1201

<A NAME="RP07008SS-8A">8a</A> Fasseur D. Rigo B. Leduk K. Cauliez P. Couturier D. J. Heterocycl. Chem. 1992, 29: 1285

<A NAME="RP07008SS-8B">8b</A> Ershov L. Granik V. Khim. Geterotsikl. Soedin. 1985, 929 ; Chem. Abstr. 1986, 104, 168389y

<A NAME="RP07008SS-9A">9a</A> Nilov D. Granik V. Izv. Akad. Nauk Ser. Khim. 2006, 1577

<A NAME="RP07008SS-9B">9b</A> Volovenko Yu. Tverdokhlebov A. Khim. Geterotsikl. Soedin. 2000, 1565

<A NAME="RP07008SS-10">10</A> Behrendt WA, Deininger R, and Schusteritz L. inventors; German Patent, DE 1171926. ; R. Zh. Khim. 1966, 8H275Π

<A NAME="RP07008SS-11">11</A> Fu J. Shuttleworth SJ. Tetrahedron Lett. 2003, 44: 3843

<A NAME="RP07008SS-12A">12a</A> Al-Mousawi SM. Mohammad MA. Elnagdi MH. J. Heterocycl. Chem. 2001, 38: 989

<A NAME="RP07008SS-12B">12b</A> Bredereck H. Effenberger F. Resemann W. Chem. Ber. 1962, 95: 2796

<A NAME="RP07008SS-13">13</A> Bachi MD. Breiman R. Meshulam H. J. Org. Chem. 1983, 48: 1439

<A NAME="RP07008SS-14">14</A> Negrebetskii V. Aleshnikova T. Prokof’eva A. Grapov A. Mel’nikov N. Zh. Obshch. Khim. 1987, 57: 1846 ; Chem. Abstr. 1988, 108, 111695y

<A NAME="RP07008SS-15">15</A> Takahata H. Takahashi K. Wang E.-Ch. Yamazaki T. J. Chem. Soc., Perkin Trans.1 1989, 1211

<A NAME="RP07008SS-16">16</A> Lacroix S. Rixhon V. Marchand-Brynaert J. Synthesis 2006, 2327

<A NAME="RP07008SS-17A">17a</A> Gugelchuk M. Hart D. Tsai Y.-M. J. Org. Chem. 1981, 46: 3671

<A NAME="RP07008SS-17B">17b</A> Celerier J. Richaud M. Lhommet G. Synthesis 1983, 195

<A NAME="RP07008SS-17C">17c</A> Singh RK. Jain S. Sinha N. Mehta A. Naqvi F. Anand N. Tetrahedron 2006, 62: 4011

<A NAME="RP07008SS-18">18</A> Sheu J. Smith M. Oeschger T. Satchell J. Org. Prep. Proced. Int. 1992, 24: 147