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A class of 2-substituted methylenedihydrobenzo[d]thiazole derivatives and their synthetic methods and applications

A kind of technology of methylene dihydrobenzene and synthetic method, applied in directions such as organic chemistry

Active Publication Date: 2022-07-05
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are many reports on the construction of aromatic benzothiazole compounds through intramolecular C-S coupling, but there are few reports on the method of synthesizing the non-aromatic dihydrobenzothiazole compounds.

Method used

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  • A class of 2-substituted methylenedihydrobenzo[d]thiazole derivatives and their synthetic methods and applications
  • A class of 2-substituted methylenedihydrobenzo[d]thiazole derivatives and their synthetic methods and applications
  • A class of 2-substituted methylenedihydrobenzo[d]thiazole derivatives and their synthetic methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Dimethyl 2-(methyl(phenyl)carbamoyl)malonate (56.2 mg, 0.2 mmol), anhydrous cobalt bromide (4.4 mg, 0.02 mmol), DDQ (90.8 mg, 0.4 mmol) were added To the reaction flask, add 4 mL of anhydrous acetonitrile, react at room temperature for 4 hours, TLC detects that the raw materials are completely consumed, add saturated sodium thiosulfate solution (4 mL) to quench the reaction, extract the organic phase with dichloromethane, and then use saturated carbonic acid. The organic phase was washed twice with sodium hydrogen solution, the organic phase was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography to obtain 55.1 mg of pure product whose structure was shown in formula (2-1), and the yield was 99%. NMR 1 H NMR, 13 CNMR spectrum such as figure 1 As shown, the product: 1 HNMR (500MHz, CDCl 3 )δ7.60(dd,J=7.8,0.5Hz,1H),7.41–7.37(m,1H),7.23(ddd,J=13.8,10.4,4.5Hz,2H),3.84(s,6H),3.50 (s,3H). 13 C NMR (126MHz, C...

Embodiment 2

[0040]

[0041] The experimental method of this example is basically the same as that of Example 1. The raw material used in this example is dimethyl 2-((4-methoxyphenyl)(methyl)carbamoyl)malonate. The reaction time was 5 hours, and the obtained product was shown in structural formula (2-2). Yield was 91%. NMR 1 H NMR, 13 C NMR spectrum as figure 2 As shown, the product: 1 HNMR (500MHz, CDCl 3 )δ7.39(s,1H),7.18(dd,J=8.3,0.7Hz,1H),7.09(d,J=8.3Hz,1H),3.83(s,6H),3.48(s,3H), 2.41(s,3H). 13 C NMR (126MHz, CDCl 3)δ167.42,167.10,139.54,133.85,127.55,127.42,121.80,111.09,87.14,51.76,37.30,21.04.

[0042] HRMS(EI)m / z calculated for C 14 H 15 NO 5 S[M] + 309.0671, found 309.0673.

Embodiment 3

[0044]

[0045] The experimental method of this example is basically the same as that of Example 1. The raw material used in this example is dimethyl 2-(methyl(p-tolyl)carbamoyl)malonate, and the reaction time is 4 hours at room temperature, so The obtained product is shown in structural formula (2-3). The yield was 87%. NMR 1 H NMR, 13 C NMR spectrum as image 3 As shown, the product: 1 H NMR (500MHz, CDCl 3 )δ7.31(s,1H),7.10(d,J=8.3Hz,1H),7.01(d,J=8.3Hz,1H),3.75(s,6H),3.39(s,3H),2.33( s, 3H). 13 C NMR (126MHz, CDCl 3 )δ167.40,167.06,139.52,133.83,127.54,127.40,121.78,111.08,87.14,51.75,37.29,21.03.

[0046] HRMS(EI)m / z calculated for C 14 H 15 NO 4 S[M] + 293.0722, found 293.0724.

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Abstract

The invention discloses a class of 2-substituted methylene dihydrobenzo[d]thiazole derivatives and a synthesis method thereof. N-alkyl / N-aryl thioamide derivatives represented by formula (1) As raw materials, in the presence of an oxidant and a catalyst, in an organic solvent, under mild reaction conditions, intramolecular enethiol interconversion occurs, and then a C-S coupling dehydrogenation coupling reaction occurs in series to obtain the described 2-Substituted methylene dihydrobenzo[d]thiazole derivatives. The synthesis method of 2-substituted methylene dihydrobenzo[d]thiazole derivatives of the present invention is controlled by conditions, has the advantages of mild conditions, economical atomic steps, high yield, high chemical selectivity and high regioselectivity , has broad application prospects. The invention also discloses the application of the 2-substituted methylene dihydrobenzo[d]thiazole derivatives in medicine and material science.

Description

technical field [0001] The invention belongs to the fields of synthetic medicine and chemical industry, and mainly relates to a class of 2-substituted methylene dihydrobenzo[d]thiazole derivatives and a synthesis method and application thereof. Background technique [0002] Benzo-heterocyclic bicyclic compounds exist widely in nature, especially heterocyclic structures containing N, O, S and other elements are common in natural products and biologically active molecules. Both benzothiazole and dihydrobenzothiazole are special bicyclic heterocyclic substances containing both N and S elements, which are widely used in medicine and materials science. At present, there are many reports on the construction of aromatic benzothiazoles by intramolecular C-S coupling, but there are few reports on the synthesis of the non-aromatic dihydrobenzothiazoles. SUMMARY OF THE INVENTION [0003] The object of the present invention is a class of 2-substituted methylene dihydrobenzo[d]thiazol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/64C07D277/84C07D513/04
CPCC07D277/64C07D277/84C07D513/04
Inventor 姜丽琴姚智杨俊蔡忠良于淼
Owner EAST CHINA NORMAL UNIV
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