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Synthesis 2019; 51(16): 3160-3170
DOI: 10.1055/s-0037-1611575
paper
© Georg Thieme Verlag Stuttgart · New York

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
a   Catalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India
,
Harika Chada
b   Loyola Academy Degree & P. G College, Old Alwal, Secunderabad, Telangana 500010, India   Email: sharada@iith.ac.in
,
Sonali Biswal
a   Catalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India
,
Sonika Sharma
b   Loyola Academy Degree & P. G College, Old Alwal, Secunderabad, Telangana 500010, India   Email: sharada@iith.ac.in
,
Duddu S. Sharada  *
a   Catalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India
› Author AffiliationsWe gratefully acknowledge the Council of Scientific and Industrial Research (CSIR 02(0297)/17/EMR-II), New Delhi, India and the Indian Institute of Technology Hyderabad (IITH) for financial support. S.M.P. thanks UGC and S.B. thanks CSIR, New Delhi, India for the award of a research fellowship.
Further Information

Publication History

Received: 05 January 2019

Accepted after revision: 19 March 2019

Publication Date:
15 April 2019 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611484.
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