Copper-Catalyzed Intramolecular α-C–H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis

Srilaxmi M. Patel; Harika Chada; Sonali Biswal; Sonika Sharma; Duddu S. Sharada

doi:10.1055/s-0037-1611575

Synthesis, Table of Contents

Synthesis 2019; 51(16): 3160-3170
DOI: 10.1055/s-0037-1611575

paper

Copper-Catalyzed Intramolecular α-C–H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis

Srilaxmi M. Patel

^aCatalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India

,

Harika Chada

^bLoyola Academy Degree & P. G College, Old Alwal, Secunderabad, Telangana 500010, India Email: sharada@iith.ac.in

,

Sonali Biswal

^aCatalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India

,

Sonika Sharma

^bLoyola Academy Degree & P. G College, Old Alwal, Secunderabad, Telangana 500010, India Email: sharada@iith.ac.in

,

Duddu S. Sharada *

^aCatalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India

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Abstract

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Abstract

A copper-catalyzed intramolecular α-C–H amination has been developed for the synthesis of quinazolin-4(3H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3H)-one was synthesized from 2-amino-N-isopropylbenzamide by C–C bond cleavage, and N-benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1H)-one along with 2-phenylquinazolin-4(3H)-one by N–C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3H)-one by copper-catalyzed intramolecular C–H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.

Key words

intramolecular C-H amination - ring-opening cyclization - rutaecarpine - quinazolin-4(3H)-one - 2-methylquinazolin-4(3H)-one

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References

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