Microwave-assisted synthesis of novel N-(4-phenylthiazol-2-yl)-benzo[d]thiazole-, thiazolo[4,5-b]pyridine-, thiazolo[5,4-b]pyridine- and benzo[d]oxazole-2-carboximidamides inspired by marine topsentines and nortopsentines

作者：Deau Emmanuel; Dubouilh Benard Carole; Levacher Vincent; Besson Thierry^*

来源：Tetrahedron, 2014, 70(35): 5532-5540.

DOI：10.1016/j.tet.2014.06.102

• Benzo[d]thiazoles
• Thiazolopyridines
• Benzo[d]oxazoles
• Microwave-assisted chemistry
• Copper-mediated cyclisation

We report the synthesis of novel N-(4-phenyithiazol-2-yl)-substituted benzo[d]thiazole-, thiazolo[4,5-b] pyridine-, thiazolo[5,4-b]pyridine- and benzo[d]oxazole-2-carboximidamides, which were inspired by marine topsentines and nortopsentines. Condensation of 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) with various ortho-halogenated anilines, aminopyridines and aminophenols gave the corresponding aryliminodithiazoles in good to excellent yields. Copper(I)-mediated or nucleophilic-assisted cyclization of aryliminodithiazoles furnished cyano-functionalized benzo[d]thiazoles, thiazolo[4,5-b]- and thiazolo [5,4-b)]-pyridines and benzo[d]oxazoles. The latter were condensed with substituted 4-phenylthiazol-2-amines to furnish twenty seven new polyaromatic carboximidamides in moderate to good yields.

• 出版日期2014-9-2