Silver‐Catalyzed Three‐Component Coupling Reaction of Amines, 2‐Isocyanobenzaldehydes, and 2,2,2‐Trifluorodiazoethane and Synthesis of Trifluoromethyl‐Substituted Indolo[1,2‐c]quinazolines

A silver‐catalyzed three‐component coupling reaction of amines, 2‐isocyanobenzaldehydes, and 2,2,2‐trifluorodiazoethane has been developed. This reaction provides an efficient method for the construction of CF3‐containing dihydroquinazolines. On the basis of this reaction, using trifluorodiazoethyl‐...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 363; no. 1; pp. 244 - 250
Main Authors Meng, Xiang‐He, Yang, Ming, Peng, Ju‐Yin, Zhao, Yu‐Long
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 05.01.2021
Subjects
2,2,2-Trifluorodiazoethane
2-Isocyanobenzaldehydes
Amines
Chemistry
Chemistry, Applied
Chemistry, Organic
Dihydroquinazolines
Indolo[1,2-c]quinazolines
Physical Sciences
Science & Technology
CASCADE CYCLIZATION REACTIONS
Amines
ENANTIOSELECTIVE SYNTHESIS
ONE-POT SYNTHESIS
SELECTIVE C-H
EFFICIENT SYNTHESIS
BOND FUNCTIONALIZATION
DIAZO-COMPOUNDS
Indolo[1,2-c] quinazolines
3+2 CYCLOADDITION
2,2,2-Trifluorodiazoethane
CARBENE INSERTION
REGIOSELECTIVE SYNTHESIS
2-Isocyanobenzaldehydes
Dihydroquinazolines
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Summary:A silver‐catalyzed three‐component coupling reaction of amines, 2‐isocyanobenzaldehydes, and 2,2,2‐trifluorodiazoethane has been developed. This reaction provides an efficient method for the construction of CF3‐containing dihydroquinazolines. On the basis of this reaction, using trifluorodiazoethyl‐substituted dihydroquinazolines as synthons, trifluoromethyl‐substituted indolo[1,2‐c]quinazolines were prepared in high yields via a TBHP/KI‐mediated sequential intramolecular cyclization and aromatization process.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000957