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α‐Diazo‐β‐oxosulfones as Partners in the Wolff 1,2,3‐Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines
Author(s) -
Safrygin Alexander,
Dar'in Dmitry,
Kantin Grigory,
Krasavin Mikhail
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900698
Subject(s) - wolff rearrangement , ketene , chemistry , diazo , acetanilide , aniline , sulfonyl , medicinal chemistry , lewis acids and bases , combinatorial chemistry , organic chemistry , catalysis , alkyl
The readily available α‐diazo‐β‐oxosulfones have been employed, for the first time, in the Wolff cyclocondensation with aromatic amines promoted by 1.5‐fold excess of TiCl 4 . The reaction was found to be general (as illustrated by 15 product examples) and resulted in moderate yields of medicinally relevant sulfonyl 1,2,3‐triazoles. Excluding the Lewis acid promoter resulted in a clean and high‐yielding formation of α‐sulfonyl acetanilides resulting from the thermal Wolff rearrangement and trapping of the ketene intermediate with an aniline molecule.