Synlett

Reversion of Paal-Knorr synthesis: A new strategy for ring-opening and N-substituent change in 1H-pyrroles

R Zamora, FJ Hidalgo

Index: Zamora, Rosario; Hidalgo, Francisco J. Synlett, 2006 , # 9 p. 1428 - 1430

Full Text: HTML

Citation Number: 5

Abstract

Abstract 1H-Pyrroles were converted into 1, 4-dicarbonyl compounds, and then into 1H- pyrroles with a different N-substituent by heating at 110 C under nitrogen in 0.3 M sodium citrate buffer, pH 3, and in the presence of alkyl or aryl amines. The new pyrroles were obtained in low to very high yields depending upon the pH, the reaction time, the initial pyrrole and amine involved, and the proportion between both reagents.

Related Articles:

Organic reactions in ionic liquids: a simple and highly regioselective N-substitution of pyrrole

[Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qin-Guo Synthesis, 2004 , # 12 p. 1951 - 1954]

Phase-transfer alkylation of heterocycles in the presence of 18-crown-6 and potassium tert-butoxide

[Guida, Wayne C.; Mathre, David J. Journal of Organic Chemistry, 1980 , vol. 45, # 16 p. 3172 - 3176]

An efficient and rapid synthesis of N-substituted pyrroles by microwave assisted solid acid catalysis

[Abid, Mohammed; Landge, Shainaz M.; Toeroek, Bela Organic Preparations and Procedures International, 2006 , vol. 38, # 5 p. 495 - 500]

Selective alkylation of pyrrole by phase transfer catalysis in the absence of solvent

[Diez-Barra, E.; Hoz, A. de la; Loupy, A.; Sanchez-Migallon, A. Journal of Heterocyclic Chemistry, 1994 , vol. 31, # 6 p. 1715 - 1718]

A new facile approach to N-alkylpyrroles from direct redox reaction of 4-hydroxy-L-proline with aldehydes

[Zou, Zhiqin; Deng, Zejun; Yu, Xinhong; Zhang, Manman; Zhao, Sihan; Luo, Ting; Yin, Xin; Xu, Hui; Wang, Wei Science China Chemistry, 2012 , vol. 55, # 1 p. 43 - 49]

More Articles...