Tetrahedron

Efficient synthesis of N-alkyl-2, 7-dihalocarbazoles by simultaneous carbazole ring closure and N-alkylation

D Výprachtický, I Kmínek, V Pokorná, V Cimrová

Index: Vyprachticky, Drahomir; Kminek, Ivan; Pokorna, Veronika; Cimrova, Vera Tetrahedron, 2012 , vol. 68, # 25 p. 5075 - 5080

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Citation Number: 4

Abstract

The N-alkyl-2, 7-dihalocarbazole as the main product was formed by the reaction of 4, 4′- dihalo-2-nitrobiphenyl with aromatic nitro compound and trialkyl phosphite. The presence and crucial role of aromatic nitro compound causes simultaneous carbazole ring closure and N-alkylation unlike the Cadogan ring closure where non-alkylated carbazole is formed as a main product. In addition, the mixture of aromatic nitro compound and trialkyl ...