Microwave-assisted synthesis of 3-formyl substituted imidazo[1,2-a]pyridines
An efficient, metal-free method for the synthesis of 3-formyl imidazo[1,2-a]pyridines is reported. The method utilises commercially available substrates and features a broad substrate scope. The intermediate enamine was isolated and a plausible reaction mechanism proposed.
Kusy, Damian,Maniukiewicz, Waldemar,B?a?ewska, Katarzyna M.
supporting information
(2019/10/16)
Synthese et Reactions SRN1 en Serie 3-Nitroimidazopyrimidine
A new heterocyclic reductive alkylating agent, 2-chloromethyl-3-nitroimidazopyrimidine, is synthesized for the first time and shown to react under phase-transfer catalysis conditions with 2-nitropropane anion to give good yield of the C-alkylated derivative.Elimination of nitrous acid allows to obtain a new class of imidazopyrimidine derivatives bearing a trisubstituted ethylenic bond in the 2 position.The SRN1 mechanism of C-alkylation is confirmed by classical inhibition experiments by dioxygen, p-dinitrobenzene or TEMPO.
Roubaud, Christine,Vanelle, Patrice,Maldonado, Jose,Crozet, Michel P.
p. 9643 - 9656
(2007/10/02)
Pyrrolization processes of vinyl substituted imidazo[1,2-a]pyridine, pyrimidine and 1,8-naphthyridine
CERTAIN 1,4-DIHYDRO-2,6-DI-LOWER HYDROCARBYL-4-HETEROCYCLIC-3,5-PYRIDINE DICARBOXYLATES WHICH ARE USEFUL AS CALCIUM CHANNEL BLOCKERS
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(2008/06/13)
C-3 Hydroxylation of Some Imidazoazines
Reactions of imidazopyridine, pyrimidine and pyrazine (1)-(3) with formaldehyde or acetaldehyde give the corresponding alcohols and secondary products characterized by 1H and 13C n.m.r.X-Ray crystallographic analysis confirms the structure of (6).The two-step sequence of n-butyllithium and reaction with aldehydes with (2)-(3) does not lead to the alcohols but to n-butyl derivatives with substituents at C(7) and C(8) respectively.
Teulade, Jean C.,Bonnet, Pierre A.,Rieu, Jean N.,Viols, Henry,Chapat, Jean P.,et al.
p. 1842 - 1874
(2007/10/02)
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