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Synthetic process of tetrazolo[1,5-a]thiapyrano[3,4-d]pyrimidine derivative

A kind of technology of pyrimidine derivative and synthesis method, applied in the field of organic synthesis, can solve the problems such as lack of tetrazole

Inactive Publication Date: 2012-03-28
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tetrazolopyrimidine derivatives inhibit the growth of microorganisms and anti-cell proliferation (Gein, V.L.; Zamaraeva, T.M.; Kurbatova, A.A.; Voronina, E.V.; ​​Vakhrin, M.I.Pharm.Chem.J.2010, 44, 366; Hussein, A.M.; Ahmed, O.M.Bioorg.Med.Chem.2010, 78, 2639.), but there has been a lack of synthetic methods for tetrazolo[1,5-a]thiapyrano[3,4-d]pyrimidine derivatives

Method used

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  • Synthetic process of tetrazolo[1,5-a]thiapyrano[3,4-d]pyrimidine derivative
  • Synthetic process of tetrazolo[1,5-a]thiapyrano[3,4-d]pyrimidine derivative

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Embodiment 1

[0008] Preparation of 9-(4-bromophenyl)-7,9-dihydro-4H-tetrazolo[1,5-a]thiapyrano[3,4-d]pyrimidin-8(5H)-one: In 10 ml of acetic acid, add 1 mmol of 4-bromobenzaldehyde (0.18 g), 1 mmol of 3-amino-1,2,4-triazole (0.09 g) and 1 mmol of 2H-thiopyran- 3,5(4H,6H)-diketone (0.13g), reacted at 25°C for 8 hours, followed by TLC monitoring, after the reaction, pour the reaction solution into 20mL of water, filter, wash the filter cake with a small amount of water, and dry After recrystallization with N,N-dimethylformamide, the corresponding 9-(4-bromophenyl)-7,9-dihydro-4H-tetrazolo[1,5-a]thiopyrano[ 3,4-d]pyrimidin-8(5H)-one (0.30 g, 82% yield). This product is colorless powder, melting point: 260-262℃.

[0009] The reaction raw materials, reaction conditions and productive rate of embodiment 1-12 are shown in Table 1.

[0010] The reaction raw material of table 1 embodiment 1-21, reaction condition and productive rate

[0011]

[0012] It can be seen from the table that the me...

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Abstract

The invention relates to a synthetic process of a tetrazolo[1,5-a]pyrano[3,4-d]pyrimidine derivative, and concretely relates to a synthetic process of a 9-aryl-7,9-dihydrogen-4H-tetrazolo[1,5-a]thiapyrano[3,4-d]pyrimidine-8(5H)-one derivative. The 9-aryl-7,9-dihydrogen-4H-tetrazolo[1,5-a]thiapyrano[3,4-d]pyrimidine-8(5H)-one derivative is generated by carrying out a three-component one-kettle-way one-step process on an aryl aldehyde, 5-aminotetrazole and 2H-thiapyran-3,5(4H,6H)-dione which are treated as raw materials in acetic acid. The process of the invention has the advantages of simple route, mild condition, and realization of the total yield of more than 60%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a synthesis method of tetrazolo[1,5-a]thiapyrano[3,4-d]pyrimidine derivatives. Background technique [0002] Thipyran and fused thiopyran derivatives have important physiological and pharmacological activities, such as herbicide, anticancer, insecticide (Scutt, J.N.; Mathews, C.J.WO Patent 2, 009, 150, 094, 2009, Chem.Abstr.2010 , 152, 66011; Dalla Via, L.; Marciani Magno, S.; Gia, O.; Marini, A.M.; Da Settimo, F.; Salerno, S.; La Motta, C.; Simorini, F.; S.; Lavecchia, A.; Di Giovanni, C.; Brancato, G.; Barone, V.; Muehlebach, M. WO Patent 2, 009, 150, 095, 2009, Chem. Abstr. 2010, 152, 51011.). Therefore, such compounds have always been a focus of attention of chemists and pharmaceutical scientists. Tetrazolopyrimidine derivatives inhibit the growth of microorganisms and anti-cell proliferation (Gein, V.L.; Zamaraeva, T.M.; Kurbatova, A.A.; Voronina, E.V.; ​​Vakhrin,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/14
Inventor 姚昌盛于晨侠李团结
Owner XUZHOU NORMAL UNIVERSITY