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Synthesis and crystal structures of three new benzotriazolylpropanamides.

ABSTRACT: The base-catalyzed Michael addition of 2-methyl-acryl-amide to benzotriazole afforded 3-(1H-benzotriazol-1-yl)-2-methyl-propanamide, C₁₀H₁₂N₄O (1), in 32% yield in addition to small amounts of isomeric 3-(2H-benzotriazol-2-yl)-2-methyl-propanamide, C₁₀H₁₂N₄O (2). In a similar manner, 3-(1H-benzotriazol-1-yl)-N,N-di-methyl-propanamide, C₁₁H₁₄N₄O (3), was prepared from benzotriazole and N,N-di-methyl-acryl-amide. All three products have been structurally characterized by single-crystal X-ray diffraction. The crystal structures of 1 and 2 comprise infinite arrays formed by N-H?O and N-H?N bridges, as well as ?-? inter-actions, while the mol-ecules of 3 are aggregated to simple ?-dimers in the crystal.

SUBMITTER: Amenta DS

PROVIDER: S-EPMC5458315 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Synthesis and crystal structures of three new benzotriazolylpropanamides.

Amenta Donna S DS Liebing Phil P Biero Julia E JE Sherman Robert J RJ Gilje John W JW Edelmann Frank T FT

Acta crystallographica. Section E, Crystallographic communications 20170526 Pt 6

The base-catalyzed Michael addition of 2-methyl-acryl-amide to benzotriazole afforded 3-(1H-benzotriazol-1-yl)-2-methyl-propanamide, C10H12N4O (1), in 32% yield in addition to small amounts of isomeric 3-(2H-benzotriazol-2-yl)-2-methyl-propanamide, C10H12N4O (2). In a similar manner, 3-(1H-benzotriazol-1-yl)-N,N-di-methyl-propanamide, C11H14N4O (3 ...[more]

PMID: 28638650

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