Synthesis and Regioselective N‐2 Functionalization of 4‐Fluoro‐5‐aryl‐1, 2, 3‐NH‐triazoles. Issue 46 (6th December 2017)

• Record Type: Journal Article
• Authors: Motornov, Vladimir A.; Tabolin, Andrey A.; Novikov, Roman A.; Nelyubina, Yulia V.; Ioffe, Sema L.; Smolyar, Ivan V.; Nenajdenko, Valentine G.
• Is Part Of: European journal of organic chemistry. Issue 46(2017)
• Page Start: 6851
• Page End: 6860
• Publication Date: 2017-12-06
• Subjects: Fluorinated heterocycles -- Nitrogen heterocycles -- Regioselectivity -- Cycloaddition -- Nitroalkenes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701338
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A new efficient synthetic route to 4‐fluoro‐5‐aryl‐1, 2, 3‐N H ‐triazoles was elaborated. The reactions of NaN3 with aryl‐substituted α‐fluoronitroalkenes resulted in the domino construction of the target fluorinated triazoles. Sulfamic acid is an effective promoter for this heterocyclization. The subsequent functionalization reactions of the obtained triazoles proceed highly regioselectively at the N‐2 position. The observed regioselectivity was supported by DFT calculations. Abstract : Efficient syntheses of 4‐fluoro‐5‐aryl‐1, 2, 3‐N H ‐triazoles are elaborated through the reactions of NaN3 with aryl‐substituted α‐fluoronitroalkenes. The subsequent functionalization reactions of the obtained triazoles proceed highly regioselectively at the N‐2 position. The observed regioselectivity is supported by DFT calculations.