Synthesis 2016; 48(08): 1159-1166
DOI: 10.1055/s-0035-1561301
paper
© Georg Thieme Verlag Stuttgart · New York

Aryliminophosphoranes as Key Intermediates in the One-Pot Synthesis­ of 1-Aryl-1,3-dihydro-2H-benzimidazol-2-ones from N-Aryl-2-nitrosoanilines and Carbon Dioxide under Mild Metal-Free Conditions

Emilia Łukasik
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland   Email: zbigniew.wrobel@icho.edu.pl
,
Zbigniew Wróbel*
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland   Email: zbigniew.wrobel@icho.edu.pl
› Author Affiliations
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Publication History

Received: 23 October 2015

Accepted after revision: 27 November 2015

Publication Date:
07 January 2016 (online)


Abstract

A new and convenient protocol is presented for the synthesis of 1-arylbenzimidazol-2-ones by a one-pot reaction of N-aryl-2-nitrosoanilines using solid carbon dioxide as a source of the key carbonyl moiety. The metal-free process is carried out under mild conditions and is compatible with a variety of substituents. The atom economy of the synthesis of the starting nitrosoanilines, accomplished by substitution of hydrogen, makes the entire synthesis of the target compounds environmentally friendly.

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