Unprecedented Cu-Catalyzed Coupling of Internal 1,3-Diynes with Azides: One-Pot Tandem Cyclizations Involving 1,3-Dipolar Cycloaddition and Carbocyclization Furnishing Naphthotriazoles

作者：Mandadapu Anil K; Sharma Sudhir K; Gupta Sahaj; Krishna Deevi G Venkata; Kundu Bijoy^*

来源：Organic Letters, 2011, 13(12): 3162-3165.

DOI：10.1021/ol201092k

A one-pot protocol for the synthesis of triazole-annulated polyheterocycles via metal-catalyzed coupling of internal 1,4-disubstituted 1,3-diynes and organic azides has been described. The mechanistic rationale for the reaction suggests tandem cyclizations involving copper-catalyzed cycloaddition and 6-endo carbocyclization reactions. The cascade cyclization leads to an increase in molecular complexity to furnish naphtho[1,2-d]triazoles in satisfactory yields. The generality of the method has been demonstrated by using a series of aromatic/aliphatic azides and symmetrical internal 1,3-diynes.

• 出版日期2011-6-17