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A kind of 2,3-dihydropyranothiazole derivatives and preparation method thereof

A technology for dihydropyranothiazoles and derivatives, which is applied in the field of pyranothiazole derivatives and their preparation, can solve problems such as unreported methods, and achieve increased diversity, high stereoselectivity and enantioselectivity. selective effect

Inactive Publication Date: 2018-02-09
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There have been many reports on the synthesis of pyranothiazole derivatives, but the method of synthesizing them by phosphine-catalyzed [4+2] cycloaddition reaction has not been reported.

Method used

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  • A kind of 2,3-dihydropyranothiazole derivatives and preparation method thereof
  • A kind of 2,3-dihydropyranothiazole derivatives and preparation method thereof
  • A kind of 2,3-dihydropyranothiazole derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] With 0.0265g (0.100mmol) compound 1a, 0.0303g (0.150mmol) compound 2a, Put MS100mg and 1mL toluene into a dry 15mL Shrek tube, add 2.00mg (0.010mmol) methyl diphenylphosphine and mix well to carry out cycloaddition reaction. In this reaction system, the molar ratio of compound 1a to compound 2a is 1: 1.5, and organophosphorus catalyst I accounts for 10% of the molar percentage of compound 1a, and is stirred at 40° C. for 2 hours, and concentrated with a rotary evaporator to pass through the column (acetic acid Ethyl ester:petroleum ether=1:20, v / v), to obtain 35.0 mg of product 3aa, with a yield of 75%.

Embodiment 2

[0029]

[0030] With 0.0265g (0.100mmol) compound 1a, 0.0303g (0.150mmol) compound 2a, Put MS100mg and 1mL toluene into a dry 15mL Shrek tube, add 1.39mg (0.010mmol) dimethylphenylphosphine and mix well to carry out cycloaddition reaction. In this reaction system, the molar ratio of compound 1a to compound 2a is 1: 1.5, and organophosphorus catalyst I accounts for 10% of the molar percentage of compound 1a, and is stirred at 40° C. for 2 hours, and concentrated with a rotary evaporator to pass through the column (acetic acid Ethyl ester:petroleum ether=1:20, v / v), to obtain 37.4 mg of product 3aa, with a yield of 80%.

Embodiment 3

[0032]

[0033] With 0.0265g (0.100mmol) compound 1a, 0.0303g (0.150mmol) compound 2a, Put MS100mg and 1mL toluene into a dry 15mL Shrek tube, add 2.10mg (0.010mmol) tributylphosphine and mix well for cycloaddition reaction. In this reaction system, the molar ratio of compound 1a to compound 2a is 1: 1.5, and organophosphorus catalyst I accounts for 10% of the molar percentage of compound 1a, and is stirred at 40° C. for 2 hours, and concentrated with a rotary evaporator to pass through the column (acetic acid Ethyl ester:petroleum ether=1:20, v / v), to obtain 21.0mg of product 3aa, yield 45%.

[0034]It can be seen from the above that the effect is very good when dimethylphenylphosphine is selected as the catalyst for the synthesis of compound 3. The 3aa NMR data are as follows:

[0035] 1 H NMR (300MHz, CDCl 3 )δ7.96-7.86 (m, 2H), 7.48-7.40 (m, 3H), 7.35-7.29 (m, 5H), 7.28-7.15 (m, 5H), 4.38-4.28 (q, J=7.1Hz, 1H), 4.14-4.04(m, 2H), 3.97(q, J=7.1Hz, 2H), 3.86-3.76(m, ...

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Abstract

The invention discloses 2,3-dihydropyranothiazole derivatives and a preparation method thereof. The preparation method comprises the following steps: in a dry Schlenk tube, uniformly mixing a first compound and allenoate in a solvent, adding an organic phosphine catalyst, stirring, and carrying out cycloaddition reaction to obtain the derivatives. The invention provides a simple and feasible novel method for synthesizing pyranothiazole derivatives. The required raw materials can be prepared by simple reaction, and thus, are low in price. The synthetic compounds are not reported in the documents, and are all new compounds. The method is implemented by carrying out cycloaddition reaction under the catalytic action of phosphine without the action of transition metals, and thus, avoids metal residues. Meanwhile, the cycloaddition reaction belongs to atomic economic reaction.

Description

technical field [0001] The invention relates to a class of pyranothiazole derivatives and a preparation method thereof. Background technique [0002] As we all know, cyanine dyes usually contain at least two auxochromatic nitrogen atoms, one of which is trivalent and the other is tetravalent. These two nitrogen atoms exist in two heterocyclic skeletons and are connected by conjugated carbon chains. Adding these two auxochromic nitrogen atoms into 5,6-dihydro-4-hydro-pyran(3,2d)thiazole, this new cyanine dye makes photographic emulsions sharper, clearer, and less Residual dye stains are produced (U.S. Patent Office 2, 886, 565 [P]. May 12, 1959.). In view of the excellent performance of pyranothiazole derivatives in improving the color development of optical dyes, it is of great research significance to develop new derivatives and simple synthesis methods. There have been many reports on the synthesis of pyranothiazole derivatives, but the method of synthesizing them by pho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04B01J31/02
CPCB01J31/0268C07D513/04
Inventor 肖玉梅郭红超王昌高阵阵袁春浩周磊杰
Owner CHINA AGRI UNIV
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