Journal
ORGANIC LETTERS
Volume 19, Issue 13, Pages 3568-3571Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01543
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Funding
- National Institutes of Health [CA042056]
- NSF fellowship [NSF/DGE-1346837]
- Turner B. and Lesly Starr Shelton Endowment Scholarship
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Simple and direct nucleophilic addition of secondary amines,, including imidazole; to, 1,2,3-triazine under mild reaction conditions (THF, 25-65 degrees C, 12-48 h), requiring no additives, cleanly provides beta-aminoenals 4 in good yields (21 examples, 31-79%). The reaction proceeds by amine nucleophilie addition to C4 of the 1,2,3-triazine in situ loss of N-2, and subsequent imine hydrolysis to provide 4.
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