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Enantioselective Synthesis of N-H-Free 1,5-Benzothiazepines

An enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. The reaction between 2-aminothiophenol and alpha , beta -unsaturated pyrazoleamides gave direct access to N-H-free 1,5-benzothiazepines in the pre... Full description

Journal Title: Chemistry: A European Journal January 2017, Vol.23(3), pp.554-557
Main Author: Wang, Guojin
Other Authors: Tang, Yu , Zhang, Yu , Liu, Xiaohua , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201605127
Link: http://search.proquest.com/docview/1880004305/?pq-origsite=primo
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title: Enantioselective Synthesis of N-H-Free 1,5-Benzothiazepines
format: Article
creator:
  • Wang, Guojin
  • Tang, Yu
  • Zhang, Yu
  • Liu, Xiaohua
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Synthesis (Chemistry)
  • Antidepressants
  • Pharmacology
  • Substrates
  • Synthesis
  • Drugs
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, January 2017, Vol.23(3), pp.554-557
description: An enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. The reaction between 2-aminothiophenol and alpha , beta -unsaturated pyrazoleamides gave direct access to N-H-free 1,5-benzothiazepines in the presence of a chiral N,N'-dioxide/Yb(OTf) sub(3) complex. Excellent enantioselectivities (up to 96% ee) and high yields (up to 99%) were obtained for a broad range of substrates under mild reaction conditions. This method provided a facile approach to the antidepressant drug (R)-(-)-Thiazesim. Go gentle: An enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. Excellent enantioselectivities (up to 96% ee) and high yields (up to 99%) were obtained for a broad range of substrates under mild reaction conditions. Furthermore, the reactions were applied to enable the concise synthesis of the chiral drug (R)-Thiazesim (see scheme).
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201605127
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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descriptionAn enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. The reaction between 2-aminothiophenol and alpha , beta -unsaturated pyrazoleamides gave direct access to N-H-free 1,5-benzothiazepines in the presence of a chiral N,N'-dioxide/Yb(OTf) sub(3) complex. Excellent enantioselectivities (up to 96% ee) and high yields (up to 99%) were obtained for a broad range of substrates under mild reaction conditions. This method provided a facile approach to the antidepressant drug (R)-(-)-Thiazesim. Go gentle: An enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. Excellent enantioselectivities (up to 96% ee) and high yields (up to 99%) were obtained for a broad range of substrates under mild reaction conditions. Furthermore, the reactions were applied to enable the concise synthesis of the chiral drug (R)-Thiazesim (see scheme).
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abstractAn enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. The reaction between 2-aminothiophenol and alpha , beta -unsaturated pyrazoleamides gave direct access to N-H-free 1,5-benzothiazepines in the presence of a chiral N,N'-dioxide/Yb(OTf) sub(3) complex. Excellent enantioselectivities (up to 96% ee) and high yields (up to 99%) were obtained for a broad range of substrates under mild reaction conditions. This method provided a facile approach to the antidepressant drug (R)-(-)-Thiazesim. Go gentle: An enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. Excellent enantioselectivities (up to 96% ee) and high yields (up to 99%) were obtained for a broad range of substrates under mild reaction conditions. Furthermore, the reactions were applied to enable the concise synthesis of the chiral drug (R)-Thiazesim (see scheme).
doi10.1002/chem.201605127
urlhttp://search.proquest.com/docview/1880004305/
date2017-01-12