Synthesis of 7-(2-(dimethylamino)vinyl)-pyrazolo[1,5-а]pyrimidine-6-carbonitriles and their heterocyclizations with N1 synthons

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Abstract

The possibility of using new 7-methylazolo[1,5-a]pyrimidine-6-carbonitriles for the construction of heterocyclic systems annulated at the pyrimidine ring has been demonstrated. Cascade cyclizations are carried out by intermediate preparation of dimethylaminovinyl derivatives. The peculiarity of using ammonia or aliphatic amines as N1 synthons in cascade reactions, depending on the process conditions used, is shown.

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About the authors

V. A. Polikarchuk

Voronezh State University

Author for correspondence.
Email: polikarchyk@mail.ru
Russian Federation, Universitetskaya pl., 1, Voronezh, 394006

M. S. Derkachev

Voronezh State University

Email: polikarchyk@mail.ru
Russian Federation, Universitetskaya pl., 1, Voronezh, 394006

Kh. S. Shikhaliev

Voronezh State University

Email: polikarchyk@mail.ru
Russian Federation, Universitetskaya pl., 1, Voronezh, 394006

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Supplementary files

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2. Fig. 1. Individual correlation interactions in the NOESY spectrum (a) and in the HMBC spectrum (b) of compound 9b (δ, ppm).

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3. Scheme 1. General scheme for the synthesis of 7-substituted azolopyrimidines containing an electron-withdrawing group at position 6

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4. Scheme 2. Synthesis of 3-R-7-methylpyrazolo[1,5-a]pyrimidine-6-carbonitriles 3a, b

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5. Scheme 3. Synthesis of 3-R-7-[(E)-2-(dimethylamino)vinyl]pyrazolo[1,5-a]pyrimidine-6-carbonitriles 5a, b

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6. Scheme 4. Reaction of 3-R-7-[(E)-2-(dimethylamino)vinyl]-pyrazolo[1,5-a]pyrimidine-6-carbonitriles with ammonium acetate and ammonia

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7. Scheme 5. Reaction of 3-R-7-[(E)-2-(dimethylamino)vinyl]pyrazolo[1,5-a]pyrimidine-6-carbonitriles 5a, b with amines

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