Tetrahedron

Selective mono-and di-N-alkylation of aromatic amines with alcohols and acylation of aromatic amines using Ph 3 P/DDQ

N Iranpoor, H Firouzabadi, N Nowrouzi, D Khalili

Index: Iranpoor, Nasser; Firouzabadi, Habib; Nowrouzi, Najmeh; Khalili, Dariush Tetrahedron, 2009 , vol. 65, # 19 p. 3893 - 3899

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Citation Number: 33

Abstract

Selective N-monoalkylation of aromatic amines with 1° and 2° alcohols and conversion of aromatic amines to amides are performed immediately and in excellent yields using triphenylphosphine (PPh3) and 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ) in dichloromethane at room temperature. Symmetrical and unsymmetrical N, N-dialkylation of aromatic amines are also carried out in modest yield at room temperature by this reagent ...