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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 9: 2832 - 2840

DOI: https://doi.org/10.6023/cjoc202404017

ARTICLES

NH4SCN-Promoted Formal [3＋3] Annulation for the Synthesis of 5-Arylated Pyrazolo[1,5-a]pyrimidines

  • Longlong Li ,
  • Xinyue He ,
  • Longsheng Zhou ,
  • Hengtong Qu ,
  • Chengtao Feng ,
  • Kun Xu
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  • a School of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012
    b College of Chemistry and Life Science, Beijing University of Technology, Beijing 100124
*E-mail: ;

Received date: 2024-04-11

  Revised date: 2024-05-07

  Online published: 2024-05-23

Supported by

Anhui Provincial Natural Science Foundation(2008085MB50); Education Bureau of Anhui Province(KJ2021A0598)

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Abstract

A formal [3＋3] annulation of 3-aminopyrazoles with cinnamaldehydes or cinnamyl alcohols mediated by NH4SCN has been developed. This protocol provides a practical route to construct 5-arylated pyrazolo[1,5-a]pyrimidines with high functional group tolerance. The use of NH4SCN as the cyanide anion surrogate allows the transient generation of cyanohydrin, which shifts the reactive center within cinnamaldehydes from formyl group to alkene group to realize an opposite regiocontrol comparing with previous reports.

Key words： tandem cyclization; hypervalent iodine; regioselectivity; pyrazolo[1,5-a]pyrimidine; cinnamaldehyde

Cite this article

Longlong Li , Xinyue He , Longsheng Zhou , Hengtong Qu , Chengtao Feng , Kun Xu . NH4SCN-Promoted Formal [3＋3] Annulation for the Synthesis of 5-Arylated Pyrazolo[1,5-a]pyrimidines[J]. Chinese Journal of Organic Chemistry, 2024 , 44(9) : 2832 -2840 . DOI: 10.6023/cjoc202404017

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