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Synthetic method of N-sulfonyl-3,4-dihydro-2H-1,4-thiazine

A -2H-1, synthesis method technology, applied in the field of chemical pharmaceutical and fine chemical preparation, can solve the problems such as not found, and achieve the effect of convenient preparation, difficult preparation and novel structure

Active Publication Date: 2016-06-01
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many methods for preparing thiazide compounds, but a fast and efficient method for preparing N-sulfonyl-3,4-dihydro-2H-1,4-thiazide compounds containing various substituents has not been found yet

Method used

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  • Synthetic method of N-sulfonyl-3,4-dihydro-2H-1,4-thiazine
  • Synthetic method of N-sulfonyl-3,4-dihydro-2H-1,4-thiazine
  • Synthetic method of N-sulfonyl-3,4-dihydro-2H-1,4-thiazine

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Effect test

Embodiment 1

[0028]

[0029] Take 10 ml of sealed tube, add 1 mmol of thiocycloethane 2a, 0.01 mmol of bis[(α,α,α',α',-tetramethyl-1,3-benzenedipropionate) rhodium], Add 0.1 mmol of acetic acid to 0.5 mmol of sulfonyltriazole 1a in 2 ml of toluene solution, evacuate the reaction solution under nitrogen protection, stir and react at 110 degrees Celsius for 1 hour, evaporate the solvent under reduced pressure, and wash the residue with ethyl acetate Using petroleum ether as eluent, silica gel column chromatography separation and purification, the corresponding N-sulfonyl-3,4-dihydro-2H-1,4-thiazine 3aa was obtained with a yield of 85%.

[0030] 3aa: white solid, mp: 137℃. 1 HNMR (300MHz, CDCl 3 )δ7.61(d, J=8.3Hz, 2H), 7.56(s, 1H), 7.49–7.46(m, 2H), 7.37–7.19(m, 10H), 5.58(t, J=3.0Hz, 1H ),2.98(dd,J=13.1,3.2Hz,1H),2.63(dd,J=13.1,3.2Hz,1H),2.40(s,3H). 13 CNMR (100MHz, CDCl 3 )δ144.2, 139.0, 137.8, 135.2, 129.9, 128.6, 128.4, 127.8, 127.7, 127.1, 126.2, 126.0, 117.6, 115.7, 54.5, 31.1, 2...

Embodiment 2

[0032] Take 10 ml of sealed tube, add 1 mmol of thiocycloethane 2a, 0.015 mmol of rhodium acetate (Rh 2 (OAc) 4 ) was added to 2.5 milliliters of 1,2-dichloroethane solution of 0.5 mmoles of sulfonyltriazole 1a, the reaction solution was evacuated under nitrogen protection, stirred and reacted for 5 hours at 80 degrees Celsius, and the solvent was evaporated under reduced pressure, and the residue The corresponding N-sulfonyl-3,4-dihydro-2H-1,4-thiazine 3aa was obtained by silica gel column chromatography using ethyl acetate and petroleum ether as eluents with a yield of 53%.

Embodiment 3

[0034] Take 10 ml sealed tube, add 0.5 mmol thiocycloethane 2a, 0.01 mmol bis[(α,α,α',α',-tetramethyl-1,3-benzenedipropionate) rhodium], Add 0.1 mmol of acetic acid to 0.5 mmol of sulfonyltriazole 1a in 1 ml of toluene solution, evacuate the reaction solution under nitrogen protection, stir and react at 110 degrees Celsius for 3 hours, evaporate the solvent under reduced pressure, and wash the residue with ethyl acetate Using petroleum ether as eluent, silica gel column chromatography separation and purification, the corresponding N-sulfonyl-3,4-dihydro-2H-1,4-thiazine 3aa was obtained with a yield of 49%.

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Abstract

The invention discloses a synthetic method of N-sulfonyl-3,4-dihydro-2H-1,4-thiazine and belongs to the technical field of chemical pharmacy and fine chemical engineering preparation. Sulfonyl-triazole, sulfo-cyclohexane, a metal rhodium catalyst and organic acid are utilized, and the synthetic method of N-sulfonyl-3,4-dihydro-2H-1,4-thiazine compounds is rapid, efficient and universal. According to the method, reaction operation is easy and convenient, and N-sulfonyl-3,4-dihydro-2H-1,4-thiazine can be rapidly prepared just through a one-step reaction. The reaction product is novel in structure and can not be easily prepared with other methods. The reaction raw materials sulfonyl-triazole and sulfo-cyclohexane are convenient to prepare.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy and fine chemical preparation, that is, sulfonyl triazole generates carbene under the action of rhodium catalyst and organic acid, and then reacts with thiocycloethane to quickly and efficiently generate a compound containing various substituents. N-sulfonyl-3,4-dihydro-2H-1,4-thiazides. The present invention provides a new and reliable technical route and synthesis strategy for the rapid and efficient preparation of N-sulfonyl-3,4-dihydro-2H-1,4-thiazine compounds containing various substituents. And fine chemical industry has broad application. Background technique [0002] Thiazides are an important class of organic compounds, which exist in many natural products with biological activity, and are also common skeleton structures of artificially synthesized drug molecules. Many thiazides have the effect of treating hypertension and mental diseases, so this The synthesis of quasi-compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/12C07D417/04
CPCC07D279/12C07D417/04
Inventor 徐华栋卢小龙沈美华刘雅婷王清霞
Owner CHANGZHOU UNIV
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