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

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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. / Kondratyev, Andrey S.; Shteingarts, Vitalij D.; Litvak, Vladimir V. et al.

In: Chemistry of Heterocyclic Compounds, Vol. 53, No. 12, 01.12.2017, p. 1350-1361.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{d757ed702dda4f22a1c8c606cb95ee6d,

title = "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",

abstract = "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).",

keywords = "1,4-benzothiazine, ammonia, domino reaction, heterocyclization, intramolecular aromatic nucleophilic substitution, polyfluoroarenes, primary amines, tandem reaction, 1,4-BENZOTHIAZINE, POSSIBLE ANTICANCER AGENTS, ANALOGS, NUCLEOPHILE, FLUORINATED 4H-1,4-BENZOTHIAZINES, COUPLING-CONSTANTS, REARRANGEMENT, THIOLATE ANION, MAGNETIC-RESONANCE SPECTRA, DERIVATIVES",

author = "Kondratyev, {Andrey S.} and Shteingarts, {Vitalij D.} and Litvak, {Vladimir V.} and Tretyakov, {Evgeny V.} and Tkachev, {Alexey V.}",

note = "Publisher Copyright: {\textcopyright} 2018, Springer Science+Business Media, LLC, part of Springer Nature.",

year = "2017",

month = dec,

day = "1",

doi = "10.1007/s10593-018-2217-y",

language = "English",

volume = "53",

pages = "1350--1361",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer New York",

number = "12",

}

RIS

TY - JOUR

T1 - 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

AU - Kondratyev, Andrey S.

AU - Shteingarts, Vitalij D.

AU - Litvak, Vladimir V.

AU - Tretyakov, Evgeny V.

AU - Tkachev, Alexey V.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - 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).

AB - 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).

KW - 1,4-benzothiazine

KW - ammonia

KW - domino reaction

KW - heterocyclization

KW - intramolecular aromatic nucleophilic substitution

KW - polyfluoroarenes

KW - primary amines

KW - tandem reaction

KW - 1,4-BENZOTHIAZINE

KW - POSSIBLE ANTICANCER AGENTS

KW - ANALOGS

KW - NUCLEOPHILE

KW - FLUORINATED 4H-1,4-BENZOTHIAZINES

KW - COUPLING-CONSTANTS

KW - REARRANGEMENT

KW - THIOLATE ANION

KW - MAGNETIC-RESONANCE SPECTRA

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85040915149&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/5e6a1402-4d4e-38ee-bd4c-bcf05de05fa8/

U2 - 10.1007/s10593-018-2217-y

DO - 10.1007/s10593-018-2217-y

M3 - Article

AN - SCOPUS:85040915149

VL - 53

SP - 1350

EP - 1361

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 12

ER -

ID: 9265516