- Facile synthesis of imidazo[1,2-a]pyridines via tandem reaction
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An efficient method for the synthesis of 5,6,7-trisubstituted imidazo[1,2-a]pyridines was developed. The products were obtained in good yields under mild conditions.
- Jia, Jiong,Ge, Yan-Qing,Tao, Xu-Tang,Wang, Jian-Wu
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experimental part
p. 185 - 194
(2010/06/14)
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- Aminoimidazo[1,2-a]pyridines: Regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines
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In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo[1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (±)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and α,β-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results.
- Chezal, Jean M,Moreau, Emmanuel,Chavignon, Olivier,Gaumet, Vincent,Métin, Jacques,Blache, Yves,Diez, Anna,Fradera, Xavier,Luque, Javier,Teulade, Jean C
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p. 295 - 307
(2007/10/03)
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- Heterocyclization of functionalized vinylic derivatives of imidazo[1,2-α]pyridines
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Heterocyclization of functionalized vinylic derivatives of imidazo[1,2-α]pyridines was explored experimentally and theoretically using semiempirical AM1 and ab initio methods. A range of functionalized vinylic derivatives (azido, amino, and carbodiimide groups) were prepared for conversion into pyrroloazaindoles 19-22, imidazo[1,x]-; (x=5, 6, 7, 8), [2,6]-, and [2,7]naphthyridines 28-30, 35-38 by thermal reaction. In the case of vinylic groups in the 5 position, peri annulation also was observed. The experimental and theoretical data are compared and discussed.
- Chezal,Moreau,Delmas,Gueiffier,Blache,Grassy,Lartigue,Chavignon,Teulade
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p. 6576 - 6584
(2007/10/03)
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