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Synthesis of unsymmetrical bis-heterocycles containing the imidazo[2,1-b]thiazole framework and their benzo[d]fused analogues by an acid-free Groebke–Blackburn–Bienaymé reaction

Author:
Kishore, Kranthi G., Islas-Jácome, Alejandro, Rentería-Gómez, Angel, Conejo, Alain S., Basavanag, Unnamatla M.V., Wrobel, Kazimierz, Gámez-Montaño, Rocío
Source:
Tetrahedron letters 2016 v.57 pp. 3556-3560
ISSN:
0040-4039
Subject:
chemical reactions, chemical structure, quinoline, thiazoles
Abstract:
A series of twenty three novel unsymmetrical bis-heterocycles having either imidazo[2,1-b]thiazole or benzo[d]imidazo[2,1-b]thiazole frameworks bound with chromone, quinoline, or julolidine were synthesized in good to excellent yields (82–97%) by an acid-free Groebke–Blackburn–Bienaymé reaction (GBBR) under microwave-heating conditions. Additionally, to study the acid-free GBBR mechanism (via concerted or non-concerted pathways), we performed the first computational study from Density Functional Theory (DFT) approach using the robust PCM(Toluene)[M06-2X/6-311+G(d,p)//M06-2X/6-311G(d)] level of theory, finding that only the non-concerted pathway is allowed.
Agid:
5244328