Synthesis of substituted esters of imidazoles, oxazoles, thiazoles, and diethyl pyrazine-2,5-dicarboxylate from a common acyclic precursor employing C-formylation strategy

• Published in: Tetrahedron letters Vol. 55; no. 16; pp. 2671 - 2674
• Main Authors: Khose, Goraksha, Shinde, Shailesh, Panmand, Anil, Kulkarni, Ravibhushan, Munot, Yogesh, Bandyopadhyay, Anish, Barawkar, Dinesh, Patil, Santoshkumar N.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 16.04.2014; Elsevier
• Subjects: C-formylation of glycine ethyl ester; Chemistry; Chemistry, Organic; Common acyclic precursor; Diethyl pyrazine-2,5-dicarboxylate synthesis; Esters; Glycine; Imidazole; Oxazole; Physical Sciences; Precursors; Science & Technology; Strategy; Substituted esters of imidazoles; Substituted esters of oxazoles; Substituted esters of thiazoles; Synthesis (chemistry); Tetrahedrons; Common acyclic precursor; C-formylation of glycine ethyl ester; Substituted esters of imidazoles; Diethyl pyrazine-2,5-dicarboxylate synthesis; Substituted esters of oxazoles; Substituted esters of thiazoles; OXIDATION; FACILE SYNTHESIS; Diethyl pyrazine-15-dicarboxylate synthesis
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2014.03.039

A novel synthetic route to substituted esters of imidazoles, oxazoles, thiazoles, and diethyl pyrazine-2,5-dicarboxylates via C-formylation of glycine ethyl ester hydrochloride is reported. This methodology is simple, robust, and gives good yields of different heterocyclic esters in one or two steps from a common acyclic precursor and is amenable to large scale synthesis.