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Your search keyword '"nitrochlorobutadiene"' showing total 3 results
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3 results on '"nitrochlorobutadiene"'

1. Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety

Author

Viktor A. Zapol’skii, Jan C. Namyslo, Armin de Meijere, and Dieter E. Kaufmann

Subjects
isothiazole, nitrochlorobutadiene, nitropyrazole, nucleophilic substitution, pyrimidine, small rings, Science, Organic chemistry, QD241-441
Abstract

The nitropolychlorobutadienes 3, 4 are valuable building blocks for various amination and successive heterocyclization products. Nucleophilic substitution reactions of the partially protected, bioactive amines 1, 2 with either vinyl, imidoyl or carbonyl chlorides result in the formation of the enamines 11, 12, 13, 16, 25, the amidine 6, and the amides 20, 21, respectively. In the following, cyclization to the highly functionalized pyrazoles 27, 28, pyrimidine 26 and pyridopyrimidine 24 succeeded. Deprotection of 21, 12 and 28 proved to be only partially feasible.

Published
2012
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2. Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety

Author

Dieter E. Kaufmann, Jan C. Namyslo, Viktor A. Zapol'skii, and Armin de Meijere

Subjects
pyrimidine, Pyrimidine, nitropyrazole, 010402 general chemistry, 01 natural sciences, Full Research Paper, lcsh:QD241-441, Amidine, chemistry.chemical_compound, lcsh:Organic chemistry, Nucleophilic substitution, Organic chemistry, Moiety, small rings, lcsh:Science, Amination, Isothiazole, 010405 organic chemistry, Organic Chemistry, isothiazole, 0104 chemical sciences, Hexane, Chemistry, chemistry, lcsh:Q, nitrochlorobutadiene, nucleophilic substitution
Abstract

The nitropolychlorobutadienes 3, 4 are valuable building blocks for various amination and successive heterocyclization products. Nucleophilic substitution reactions of the partially protected, bioactive amines 1, 2 with either vinyl, imidoyl or carbonyl chlorides result in the formation of the enamines 11, 12, 13, 16, 25, the amidine 6, and the amides 20, 21, respectively. In the following, cyclization to the highly functionalized pyrazoles 27, 28, pyrimidine 26 and pyridopyrimidine 24 succeeded. Deprotection of 21, 12 and 28 proved to be only partially feasible.

Published
2012

3. Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety.

Author

Zapol'skii VA, Namyslo JC, de Meijere A, and Kaufmann DE

Abstract

The nitropolychlorobutadienes 3, 4 are valuable building blocks for various amination and successive heterocyclization products. Nucleophilic substitution reactions of the partially protected, bioactive amines 1, 2 with either vinyl, imidoyl or carbonyl chlorides result in the formation of the enamines 11, 12, 13, 16, 25, the amidine 6, and the amides 20, 21, respectively. In the following, cyclization to the highly functionalized pyrazoles 27, 28, pyrimidine 26 and pyridopyrimidine 24 succeeded. Deprotection of 21, 12 and 28 proved to be only partially feasible.

Published
2012
Full Text
View/download PDF

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