Tetrahedron Letters

Facile synthesis of vicinal diamines via oxidation of N-phenyltetrahydroisoquinolines with DDQ

ASK Tsang, MH Todd

Index: Tsang, Althea S.-K.; Todd, Matthew H. Tetrahedron Letters, 2009 , vol. 50, # 11 p. 1199 - 1202

Full Text: HTML

Citation Number: 74

Abstract

The oxidation of N-phenyltetrahydroisoquinolines occurs rapidly with DDQ. Under ambient conditions and in the presence of nitromethane, the corresponding β-nitroamine derivatives are isolated in good to excellent yields. Variation in the electronic nature of the isoquinoline and the N-phenyl substituent showed that a broad range of substituents are tolerated, with electronic communication between the isoquinoline aromatic ring and the C1 carbon ...