Open AccessCycloadditions of Noncomplementary Substituted 1,2,3-Triazines
Author(s) -
Erin D. Anderson,
Adam S. Duerfeldt,
Kaicheng Zhu,
Christopher M. Glinkerman,
Dale L. Boger
Publication year - 2014
Publication title -
organic letters
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol502436n
Subject(s) - chemistry , cycloaddition , steric effects , regioselectivity , reactivity (psychology) , medicinal chemistry , polar effect , electronic effect , scope (computer science) , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , computer science , programming language
The scope of the [4 + 2] cycloaddition reactions of substituted 1,2,3-triazines, bearing noncomplementary substitution with electron-withdrawing groups at C4 and/or C6, is described. The studies define key electronic and steric effects of substituents impacting the reactivity, mode (C4/N1 vs C5/N2), and regioselectivity of the cycloaddition reactions of 1,2,3-triazines with amidines, enamines, and ynamines, providing access to highly functionalized heterocycles.
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