DMAP-promoted in situ activation of bromoacetic acid as a 2-carbon synthon for facile synthesis of pyridines and fused pyridin-2-ones. Issue 41 (13th October 2016)

• Record Type: Journal Article
• Authors: Wang, Lu; Zhu, Gaoyuan; Tang, Weifang; Lu, Tao; Du, Ding
• Is Part Of: Tetrahedron. Volume 72:Issue 41(2016)
• Page Start: 6510
• Page End: 6517
• Publication Date: 2016-10-13
• Subjects: Pyridine -- Fused pyridin-2-one -- Bromoacetic acid -- Heterocyclic synthesis -- Annulation -- GAP chemistry; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.08.062
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A general and simple synthesis of 2, 4, 6-trisubstituted pyridines and fused pyridine-2-ones from bromoacetic acid is developed via a DMAP-promoted in situ activation strategy. In this protocol, readily accessible bromoacetic acid has been effectively employed as a 2C synthon to undergo formal [2+4] cycloadditions with diverse acyclic and cyclic 1-azadienes. Low costs of the reagents and materials, mild reaction conditions and broad functional-group tolerance make this protocol applicable for practical and scalable synthesis. Graphical abstract: