Chem. J. Chinese Universities ›› 2016, Vol. 37 ›› Issue (10): 1804.doi: 10.7503/cjcu20160410

• Organic Chemistry • Previous Articles     Next Articles

Selenium-catalyzed Carbonylation of 4-Aminopyridine with Nitro Aromatics to 4-Pyridinylureas

ZHANG Xiaopeng*(), LI Zhengwei, WANG Yan, NIU Xueli, ZHANG Guisheng   

  1. Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals,Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China
  • Received:2016-06-07 Online:2016-10-10 Published:2016-08-23
  • Contact: ZHANG Xiaopeng E-mail:zhangxiaopengv@sina.com
  • Supported by:
    † Supported by the Program for Innovative Research Team in Science and Technology in University of Henan Province, China(No.15IRTSTHN003), the Young Backbone Teachers Training Fund of Education Department of Henan Province, China(No.2013GGJS-059) and the Young Backbone Teachers Training Fund of Henan Normal University, China(No.2011-8)

Abstract:

A facile, economical and environment-friendly approach to 4-pyridinylureas was reported. With cheap and easily available nonmetal selenium as the catalyst, triethylamine as the cocatalyst, carbon monoxide instead of virulent phosgene as the carbonylation reagent, the target products could be obtained via selenium-catalyzed redox carbonylation of 4-aminopyridine with nitro aromatics by bubbling of CO. The optimal reaction conditions were obtained by exploring the effects of main factors on the carbonylation reaction such as reaction temperature, reaction time, kinds of solvents and bases. Under the optimal conditions, 4-pyridinylureas could be obtained in moderate to good yields. The applicability of the substrates nitro aromatics was good. The possible reaction mechanism was also proposed at the end of this paper.

Key words: Selenium-catalysis, Carbonylation, 4-Pyridinylurea(Ed.: P, H, F, K)

CLC Number: 

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