Visible Light Driven Coupling of 2‐aminopyridines and α‐Keto Vinyl Azides for the Synthesis of Imidazo[1,  2‐a]pyridines and Their Cytotoxicity. Issue 26 (18th September 2017)

• Record Type: Journal Article
• Authors: Adiyala, Praveen Reddy; Sastry, Kasinathuni Naga Visweswara; Kovvuri, Jeshma; Nagarajan, Apoorva; Reddy, Velma Ganga; Sayeed, Ibrahim Bin; Nayak, Vedinthe Lakshma; Maurya, Ram Awatar; Kamal, Ahmed
• Is Part Of: ChemistrySelect. Volume 2:Issue 26(2017)
• Page Start: 8158
• Page End: 8161
• Publication Date: 2017-09-18
• Subjects: Vinylazides -- Imidazo[1, 2-a]pyridine -- Ru(bpy)3Cl2.6H2O -- 2H-azirine; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201700952
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: α‐Keto vinyl azides and 2‐aminopyridines were coupled to yield 1‐aryl‐ N‐( 2‐arylimidazo[1, 2‐a]pyridin‐3‐yl)methanimines in the presence of visible light using Ru(bpy)3 Cl2 .6H2 O as a photocatalyst. This synthetic protocol allows the formation of 3 new C−N bonds in the overall transformation at ambient temperature. It is applicable to a wide range of vinyl azides and 2‐aminopyridines providing a straightforward access to a variety of highly functionalized imidazo[1, 2‐a]pyridines in high yields. The synthesized imidazo[1, 2‐a]pyridines were evaluated for their cytotoxic activity against a set of four selected human cancer cell lines i.e, A549 (lung cancer), DU‐145 (prostate cancer), MCF‐7 (breast cancer) and Hela (cervical cancer). Many compounds of the series (4 e, 4 g, 4 i, 4 j and4 u ) exhibited promising cytotoxicity in these cancer cell lines. Abstract : α‐Keto vinyl azides and 2‐aminopyridines were coupled to yield 1‐aryl‐ N ‐(2‐arylimidazo[1, 2‐a]pyridin‐3‐yl)methanimines in the presence of visible light using Ru(bpy)3 Cl2 .6H2 O as a photocatalyst. This synthetic protocol allows the formation of 3 new C−N bonds in the overall transformation at ambient temperature. It is applicable to a wide range of vinyl azides and 2‐aminopyridines providing a straightforward access to a variety of highly functionalized imidazo[1, 2‐a]pyridines in high yields. The synthesized imidazo[1, 2‐a]pyridines were evaluated for their cytotoxic activity against a set of four selected human cancer cell lines.