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Direct Synthesis of ?-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.

ABSTRACT: Simple and direct nucleophilic addition of secondary amines, including imidazole, to 1,2,3-triazine under mild reaction conditions (THF, 25-65 °C, 12-48 h), requiring no additives, cleanly provides ?-aminoenals 4 in good yields (21 examples, 31-79%). The reaction proceeds by amine nucleophilic addition to C4 of the 1,2,3-triazine, in situ loss of N2, and subsequent imine hydrolysis to provide 4.

SUBMITTER: Quinones RE

PROVIDER: S-EPMC5546251 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.

Quiñones Ryan E RE Glinkerman Christopher M CM Zhu Kaicheng K Boger Dale L DL

Organic letters 20170628 13

Simple and direct nucleophilic addition of secondary amines, including imidazole, to 1,2,3-triazine under mild reaction conditions (THF, 25-65 °C, 12-48 h), requiring no additives, cleanly provides β-aminoenals 4 in good yields (21 examples, 31-79%). The reaction proceeds by amine nucleophilic addition to C4 of the 1,2,3-triazine, in situ loss of N<sub>2</sub>, and subsequent imine hydrolysis to provide 4. ...[more]

PMID: 28657329

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