ChemInform Abstract: A Mild and Efficient Route to 2‐Benzyl Tryptamine Derivatives via Ring‐Opening of β‐Carbolines.

Abstract

Indole derivatives R 0140A Mild and Efficient Route to 2-Benzyl Tryptamine Derivatives via Ring-Opening of β-Carbolines. -The route involves the synthesis of β-carbolines via a Pictet-Spengler reaction, followed by ring-opening under catalytic hydrogenation with concomitant deprotection of benzyloxy-and acetoxy-substituted derivatives. The methodology does not require the protection of the nitrogen atoms. An additional N-alkylation [cf. (IX)] allows access to N-alkyl-substituted tryptamines. -(HADJAZ, F.; YOUS, S.; LEBEGUE, N.; BERTHELOT, P.; CARATO*, P.; Tetrahedron 64 (2008) 42, 10004-10008; Lab. Chim. Ther., Fac. Pharm., F-59006 Lille, Fr.; Eng.) -Klein 08-137