Synthesis p. 1183 - 1189 (1995)
Update date:2022-08-05
Topics:
Horvath
Michael adducts of azoles (4-phenyl-, 4-methyl- and 4-nitroimidazole, 4-methylbenzimidazole, 1,2,4-triazole and theophylline) are shown to be valuable substrates for obtaining the N-substituted derivatives of the parent heterocycles by a quaternization-Hofmann elimination sequence. The effectiveness of the procedure is dependent on the regiochemical outcome of the first, N-protective step, i.e. the Michael addition. By choosing the appropriate Michael acceptor, alkylating agent and deprotection conditions, the thermodynamically less stable regioisomers of N-substituted azoles have been obtained in high yields.
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Doi:10.1016/0022-328X(95)05488-B
(1995)Doi:10.1021/jm020940p
(2002)Doi:10.1021/om950891x
(1996)Doi:10.1002/jhet.820
(2012)Doi:10.1021/jo01274a048
(1968)Doi:10.1016/0584-8539(95)01471-1
(1995)
