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Synthesis 2023; 55(20): 3303-3314
DOI: 10.1055/a-2116-5206
paper

Synthesis of Quinoline and Quinolin-2(1H)-one Derivatives via Nickel Boride Promoted Reductive Cyclization

Rumpa Sarkar
a   Department of Chemistry, Indian Institute of Engineering Science and Technology (IIEST), Shibpur, PO Botanic Garden, Howrah 711103 (WB), India
,
Surya Kanta Samanta
a   Department of Chemistry, Indian Institute of Engineering Science and Technology (IIEST), Shibpur, PO Botanic Garden, Howrah 711103 (WB), India
,
Anila M. Menon
b   Crystallography and Crystal Chemistry Laboratory, Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal 462066, India
,
Deepak Chopra
b   Crystallography and Crystal Chemistry Laboratory, Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal 462066, India
,
Debabani Ganguly
c   Centre for Health Science and Technology, JIS Institute of Advanced Studies and Research Kolkata, JIS University, India
,
Mrinal K. Bera  ∗
a   Department of Chemistry, Indian Institute of Engineering Science and Technology (IIEST), Shibpur, PO Botanic Garden, Howrah 711103 (WB), India
› Author AffiliationsFinancial support from the Science and Engineering Research Board (SERB), New Delhi, India (Grant No. CRG/2021/002889) is most gratefully acknowledged. R.S. gratefully thanks the Council of Scientific and Industrial Research, India (CSIR New Delhi) for financial support in the form of a CSIR-JRF. A.M.M. thanks the Indian Institute of Science­ Education and Research Bhopal (IISER Bhopal) for a senior research fellowship.
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Abstract

A mild and efficient approach for the synthesis of diversely substituted quinoline and quinolin-2-one derivatives is disclosed. In situ generated nickel boride proved to be an effective promoter of the reductive cyclization reaction. Broad substrate scope, mild reaction conditions, consistent yield, and a wide range of functional group tolerance are the other notable features of the newly discovered reaction. A large number of quinoline and quinolin-2-one derivatives may be prepared from milligram to multigram scale employing this intramolecular reductive cyclization protocol.

Keywords

quinolines - quinolin-2(1H)-ones - nickel boride - sodium borohydride - reductive cyclization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2116-5206.
  • Supporting Information


Publication History

Received: 15 March 2023

Accepted after revision: 22 June 2023

Accepted Manuscript online:
22 June 2023

Article published online:
07 August 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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