Synthesis of 2, 4-dihydro-3H-1, 2, 4-triazol-3-ylidene derivatives from 1, 3-Indanediones. (16th March 2021)

• Record Type: Journal Article
• Authors: Payili, Nagaraju; Rekula, Santhosh Reddy; Naidu, Challa Gangu; Yennam, Satyanarayana
• Is Part Of: Tetrahedron letters. Volume 67(2021)
• Publication Date: 2021-03-16
• Subjects: Indanedione -- 3+2 Cycloaddition -- Triazoles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.152832
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Efficient transition metal free, general and efficient two step method for flexible synthesis of 1, 2, 4-triazole was described. T3 P mediated dehydrative coupling of hydrazones by [3 + 2] cycloaddition gave 1, 2, 4-tetrazole derivatives. The new 1, 2, 4-triazole derivatives were successfully separated and characterized. Abstract: A simple and efficient synthesis has been developed for 1, 2, 4-traizole derivatives from 2-arylidene-1, 3-indandiones and 1-methylhydrazine-1-carbonitrile in two steps with good yields. The reactions include formal [3 + 2] cycloaddition and skeletal rearrangement to provide amino hydrazones followed by T3P mediated dehydrogenative coupling. This method provides a new and useful strategy for synthesis of novel 1, 2, 4-triazole derivatives.