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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/3932
Title: DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles
Authors: Bhagat U.K.
Kamaluddin
Peddinti R.K.
Published in: Tetrahedron Letters
Abstract: Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major adducts and 1,4-disubstituted 1H-1,2,3-triazoles as minor adducts. Though the reaction times are longer (4–8 days), the two regioisomers were separated by using column chromatography and the adducts were obtained in very good to excellent combined chemical yields. The electron-rich and electron-poor substituents on aryl moiety of 4-aryl-triazoles could tolerate the reaction conditions to afford the title adducts. © 2016 Elsevier Ltd
Citation: Tetrahedron Letters (2017), 58(4): 298-301
URI: https://doi.org/10.1016/j.tetlet.2016.11.125
http://repository.iitr.ac.in/handle/123456789/3932
Issue Date: 2017
Publisher: Elsevier Ltd
Keywords: Conjugate addition
Cycloalkenones
DABCO
Organobase
Triazoles
ISSN: 404039
Author Scopus IDs: 57192691572
56156571900
6602375630
Author Affiliations: Bhagat, U.K., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India
Kamaluddin, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India
Peddinti, R.K., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India
Funding Details: The authors thank Prof. U. P. Singh for collecting the single crystal X-ray data. UKB thanks MHRD, India for a research fellowship.
Corresponding Author: Peddinti, R.K.; Department of Chemistry, Indian Institute of Technology RoorkeeIndia; email: rkpedfcy@iitr.ac.in
Appears in Collections:Journal Publications [CY]

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