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

Authors

  • 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

Financial 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.


Graphical Abstract

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.

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

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