Domino reaction of (2-haloethyl)polyfluorophenyl sulfides, sulfoxides, and sulfones with ammonia or amines: one-pot synthesis of 3,4-dihydro-2H-1,4-benzothiazines polyfluorinated at the benzene ring and the corresponding 1-oxides and 1,1-dioxides

Domino reaction of (2-haloethyl)polyfluorophenyl sulfides, sulfoxides, and sulfones with ammonia or amines: one-pot synthesis of 3,4-dihydro-2H-1,4-benzothiazines polyfluorinated at the benzene ring and the corresponding 1-oxides and 1,1-dioxides Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2017, Volume: 53, Number: 12, Pages: 1350-1361 Pages count : 12 DOI: 10.1007/s10593-018-2217-y

Tags

ammonia; 1,4-benzothiazine; polyfluoroarenes; domino reaction; heterocyclization; intramolecular aromatic nucleophilic substitution; primary amines; tandem reaction

Authors

Kondratyev Andrey S. ¹ , Shteingarts Vitalij D. ¹ , Litvak Vladimir V. ² , Tretyakov Evgeny V. ^1,3 , Tkachev Alexey V. ^1,3

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Siberian Branch, Inst Chem Biol & Fundamental Med, 8 Akad Lavrentieva Ave, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova St, Novosibirsk 630090, Russia

5,7,8-Trifluoro-3,4-dihydro-2H-1,4-benzothiazine, corresponding 1-oxide and 1,1-dioxide, as well as some of their 4- and 6-substituted derivatives were prepared in 39-88% yields via the reaction of ammonia or primary aliphatic amines with (2-haloethyl)-2,3,5,6-tetrafluorophenyl sulfides, sulfoxides, or sulfones. Formation of the heterocyclic moiety was shown to proceed as a two-stage process starting from halogen replacement at the side chain followed by intramolecular aminodefluorination. The ratio of the reaction rates of the two processes depends on the nature of the reagent used. Chemical structures of the cyclization products were proved by precise analysis of the NMR spectra and by comparing the experimental NMR parameters with those calculated by an empirical additivity scheme and quantum chemistry methods (DFT).

Kondratyev A.S. , Shteingarts V.D. , Litvak V.V. , Tretyakov E.V. , Tkachev A.V.
Domino reaction of (2-haloethyl)polyfluorophenyl sulfides, sulfoxides, and sulfones with ammonia or amines: one-pot synthesis of 3,4-dihydro-2H-1,4-benzothiazines polyfluorinated at the benzene ring and the corresponding 1-oxides and 1,1-dioxides
Chemistry of Heterocyclic Compounds. 2017. V.53. N12. P.1350-1361. DOI: 10.1007/s10593-018-2217-y WOS Scopus РИНЦ

Published print:	Dec 1, 2017
Published online:	Jan 24, 2018

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