Gold(I)‐Catalyzed Post‐Ugi Hydroarylation: An Approach to Pyrrolopyridines and Azepinoindoles. Issue 12 (8th March 2013)

• Record Type: Journal Article
• Authors: Kumar, Amit; Vachhani, Dipak D.; Modha, Sachin G.; Sharma, Sunil K.; Parmar, Virinder S.; Van der Eycken, Erik V.
• Is Part Of: European journal of organic chemistry. Issue 12(2013)
• Page Start: 2288
• Page End: 2292
• Publication Date: 2013-03-08
• Subjects: Synthetic methods -- Multicomponent reactions -- Heterocycles -- Hydro­arylation -- Cyclization -- Fused‐ring systems -- Gold; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300132
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A diversity‐oriented approach comprising a Ugi four‐component reaction and gold(I)‐catalyzed hydroarylation under very mild reaction conditions has been elaborated. This gives direct access to the synthesis of biologically important heterocycles such as pyrrolopyridines, pyridoindoles, and azepinoindoles in very good yields. The influence of the nucleophilicity of the heterocycle and the mode of ring closure are discussed. Abstract : The synthesis of diversely substituted azepine‐ and pyridine‐fused pyrrole and indole heterocycles through post‐Ugi gold(I)‐catalyzed intramolecular hydroarylation is documented. The Ugi four‐component reaction generates diversity, whereas gold(I) ensures exo / endo selectivity during cyclization. This efficient synthetic methodology may provide expedient access towards biologically important heterocycles.