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Synthesis 2024; 56(01): 151-160
DOI: 10.1055/s-0042-1751636
DOI: 10.1055/s-0042-1751636
paper
Synthesis of Highly Substituted 1,2,4-Triazole-Based 3-Nitrochromanes through Aza-Michael Addition Reaction under Catalyst- and Base-Free Conditions
S.M. is thankful to the Council of Scientific and Industrial Research (CSIR) [Project no. 02(0381)/19/EMR-II] and the Science and Engineering Research Board (SERB)-SURE (Project no. SUR/2022/000257) for financial support in the form of research grants. T.D. acknowledges the Department of Science and Technology, Ministry of Science and Technology, India, INSPIRE Programme Division (Ref. DST/INSPIRE/03/2017/000193, New Delhi) for their financial support. S.P.P. acknowledges the Science & Technology Department, Government of Odisha Programme (2692/ST, Bhubaneswar, 16-07-2020). S.M. and S.N. are also thankful to the Public Health by Higher Education Department, Government of Odisha (Grant no. 26913/HED/HE-PTC-WB-02-17 OHEPEE).
Abstract
A simple and efficient aza-Michael addition reaction of 1,2,4-triazoles to functionalized 2-aryl-3-nitro-2H-chromenes has been demonstrated under catalyst- and base-free conditions. In this transformation, one intermolecular C–N bond formation is achieved at room temperature. A series of highly substituted 1,2,4-triazole-based 3-nitrochromanes were produced in good to excellent yields, up to 86%. The relative configuration of the Michael adducts was confirmed by X-ray crystallographic analysis. High yield, easy accessibility and a wide variety of functional group tolerance are the key features of this aza-Michael addition reaction.
Key words
1,2,4-triazoles - 3-nitro-2-phenyl-2H-chromenes - intermolecular aza-Michael addition reaction - polysubstituted chromanes - catalyst-free conditionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751636.
- Supporting Information
Publication History
Received: 10 June 2023
Accepted after revision: 05 September 2023
Article published online:
18 October 2023
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