Triphenylphosphine-mediated reductive cyclization of 2-nitrobiphenyls: a practical and convenient synthesis of carbazoles

AW Freeman, M Urvoy, ME Criswell

Index: Freeman, Adam W.; Urvoy, Marie; Criswell, Megan E. Journal of Organic Chemistry, 2005 , vol. 70, # 13 p. 5014 - 5019

Full Text: HTML

Citation Number: 162

Abstract

The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling ...

 Related Synthetic Route

~84%

Learn More

~%

Learn More

~%

Learn More

~82%

Learn More

~97%

Learn More

~94%

Learn More

~90%

Learn More

~%

Learn More

~%

Learn More

~89%

Learn More

~93%

Learn More

~%

Learn More

~%

Learn More

~77%

Learn More

~%

Learn More

~%

Learn More

~77%

Learn More

~%

Learn More

~%

Learn More

~77%

Learn More