Simultaneous Formation and Functionalization of Aryliminophosphoranes Using 1,3-Dihydro-1H-benzimidazol-2-ones as Precursors

An atom- and step-economic synthesis of aryliminophosphoranes bearing ortho urea was achieved via unprecedented Ph3P-I-2 mediated ring-opening of 1,3-dihydro-1H-benzimidazol-2-ones with secondary amines. Tandem aza-Wittig/heterocyclization of the functionalized aryliminophosphoranes upon treatment w...

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Published inJournal of organic chemistry Vol. 85; no. 20; pp. 13330 - 13338
Main Authors Pattarawarapan, Mookda, Yamano, Dolnapa, Wiriya, Nittaya, Yimklan, Saranphong, Phakhodee, Wong
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 16.10.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID CERAMIDASE
SULFA-MICHAEL ADDITION
ONE-POT SYNTHESIS
EFFICIENT SYNTHESIS
CHEMISTRY
AZA-WITTIG REACTION
IMINOPHOSPHORANES
INHIBITORS
DERIVATIVES
DISCOVERY
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Summary:An atom- and step-economic synthesis of aryliminophosphoranes bearing ortho urea was achieved via unprecedented Ph3P-I-2 mediated ring-opening of 1,3-dihydro-1H-benzimidazol-2-ones with secondary amines. Tandem aza-Wittig/heterocyclization of the functionalized aryliminophosphoranes upon treatment with isothiocyanates enables a facile access to a single regioisomer of N-1-substituted 2-aminobenzimidazoles as well as fused tetracyclic quinazolinone derivatives in one-pot. P-31{H-1} NMR studies suggested that the urea C-N bond of benzimidazolone is weakened by N-phosphorylation, leading to aminolysis rather than the expected deoxygenative amination.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01979