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Synthesis 2024; 56(22): 3475-3487
DOI: 10.1055/a-2368-8392
paper

Synthesis of Difluoromethyl Chromono[3,2-c]pyrazolines/pyrazoles by [3+2] Cycloaddition Reaction of Difluoroacetohydrazonoyl Bromides with 3-EWG-Chromones

Ke-Hu Wang∗
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China
,
Xiuwen Liang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China
,
Wenjing Luo
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China
,
Maizhuo Chen
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China
,
Junjiao Wang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China
,
Danfeng Huang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China
,
Yulai Hu  ∗
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China
b   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
› Author AffiliationsWe are thankful for financial support from the National Natural Science Foundation of China (22061037), State Key Laboratory of Applied Organic Chemistry, Lanzhou University, and Shanghai Sinofluoro Chemicals Co., Ltd.
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Abstract

A highly convenient and straightforward strategy for the synthesis of difluoromethyl substituted tricyclic fused chromono[3,2-c]pyrazolines/pyrazoles is developed via [3+2]-cycloaddition of difluoroacetohydrazonoyl bromides to chromene derivatives bearing an electron-withdrawing group at the 3-position. The reaction has the advantages of mild conditions, good tolerance of functional groups, and simple operation.

Key words

cycloaddition reaction - chromono[3,2-c]pyrazolines - chromono[3,2-c]pyrazoles - difluoroacetohydrazonoyl bromides - 3-EWG chromones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2368-8392.
  • Supporting Information


Publication History

Received: 02 May 2024

Accepted after revision: 17 July 2024

Accepted Manuscript online:
18 July 2024

Article published online:
12 August 2024

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