Medicinal Chemistry Division, Central Drug Research Institute, CSIR, Lucknow 226 001, India.
Org Lett. 2011 Jun 17;13(12):3162-5. doi: 10.1021/ol201092k. Epub 2011 May 17.
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.
一种通过金属催化内部 1,4-二取代 1,3-二炔和有机叠氮化物的偶联反应合成三唑并稠合多杂环的一锅法已被描述。该反应的机理理由表明涉及铜催化环加成和 6-endo 碳环化反应的串联环化。级联环化导致分子复杂性增加，以令人满意的收率得到萘[1,2-d]三唑。该方法的通用性已通过使用一系列芳香族/脂肪族叠氮化物和对称内部 1,3-二炔来证明。
