Synthesis of 3-[4-(1-Benzofuran-2-yl)-1,3-thiazol-2-yl]-2-(4-aryl)-1,3-thiazolidin-4-one Derivatives as Biological Agents

A protocol for the synthesis of 3-[4-(1-benzofuran-2-yl)-1,3-thiazol-2-yl]-2-(4-aryl)-1,3-thiazolidin-4-one derivatives (5a–e) has been developed from 1-(1-benzofuran-2-yl)-2-bromoethanone (2),which served as a key intermediate for the synthesis of the title compounds. The reaction of compound 2 with thiourea furnished 4-(1-benzofuran-2-yl)-1,3-thiazol-2-amine 3, which upon further reaction with various aromatic aldehydes, gave Schiff bases 4a–e. These Schiff bases, when treated with thioacetic acid in the presence of catalytic amount of anhydrous ZnCl₂, yielded thiazolidinone derivatives 5a–e. All the newly synthesized compounds have been characterized by analytical and spectral data and screened for their antimicrobial and analgesic activity.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

2-[4-(2-Thienyl)-1,3-thiazol-2-yl]ethanenitrile in Heterocyclic Synthesis of Biological Interist

Abstract

Thiazolylacetonitrile was used in the synthesis of coumarin, pyrazolo[4,3]pyrimidines, 1,3,4-thiadiazolines, aminothiophenes, and thiazoles in a good yields. Also, pyrazolo[4,5-d]triazolino[4,5-a]pyrimidines, pyrazolo[4,5-d]thiazolino[3,2-a]pyrimidines, and pyrazolo[4,5-d]tetrazolino[1,5-a]pyrimidines were synthesized from pyrazolo[4,5-d]pyrimidine. Structures of the newly synthesized were elucidated by elemental analysis, spectral data, and alternative synthesis routes whenever possible. Some synthesized compounds were tested for their antimicrobial activity.     

1-芳甲酰基-3-[4-((2-氰基亚胺基-1,3-噻唑烷-3-基)甲基)-噻唑-2-基]硫脲的合成及其生物活性研究

为了寻找高活性的杂环农药,将酰基硫脲骨架引入到噻唑分子结构中,设计合成了14个未见文献报道的1-取代苯甲酰基-3-[4-((2-氰基亚胺基-1,3-噻唑烷-3-基)甲基)-噻唑-2-基]硫脲类化合物.采用核磁共振氢谱和元素分析确认了新化合物的结构.初步的生物活性测试结果表明,部分标题化合物显示出一定的杀菌、植物生长调节或除草活性.     

Synthesis and Structure of (2E)-3-Aryl(hetaryl)-2-[5-bromo-4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles

Russian Journal of General Chemistry - Bromination of (2E)-3-aryl(hetaryl)-2-[4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles proceeds regioselectively at the C5 atom of the thiazole ring with the...     

A convenient method for the synthesis of 2-[(5-benzyl-1,3-thiazol-2-yl)imino]-1,3-thiazolidin-4-one derivatives

It was found that the reaction of 2-chloroacetamido/chloropropioamido-5-benzylthiazole with potassium thiocyanate gave, via rearrangement, 2-[(5-benzyl-1,3-thiazol-2-yl)imino]-1,3-thiazolidin-4-ones.     

Synthesis and molecular structure of 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazines

Reactions of some 2-hydrazinopyrimidine hydrochlorides with potassium thiocyanate gave 1-(pyrimidin-2-yl)thiosemicarbazides which underwent Hantzsch condensation with aryl chloromethyl ketones to produce 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazine hydrochlorides. The protonation was accompanied by mutually dependent tautomeric rearrangements of heterocyclic fragments.     

Synthesis of [4-amino-5-(R-benzyl)-1,3-thiazol-2-ylsulfanyl] acetic acids

Russian Journal of Organic Chemistry - (4-Amino-1,3-thiazol-2-ylsulfanyl)acetic acids were synthesized by reaction of α-thiocyanatonitriles with sulfanylacetic acid in boiling acetonitrile.     

N-[3-nitro(amino)coumarin-4-yl]anthranilic acid amides. Synthesis of 6,7,8,13-tetrahydro[1]benzopyrano[4,3-b][1,4] benzodiazepine-6,8-dione

The reaction of 3-nitro-4-chlorocoumarin with anthranilic acid was used to synthesize N-(3-nitro-4-coumarinyl)-anthranilic acid, from which, through the acid chloride, we obtained a number of amides, which were reduced to N-(3-amino-4-coumarinyl)anthranilic acid amides The latter are cyclized under the influence of hydrochloric acid to 6,7,8,13-tetrahydro[1]benzopyrano-[4,3-b][1, 4]benzodiazepine-6,8-dione, which was also obtained from N-(3-amino-4-coumarinyl)anthranilic acid by its thermolysis or treatment with hydrochloric acid.See [1] for our preliminary communication.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1208–1212, September, 1989.     

Synthesis of （S）-2-（3-Arylacrylamido）-3-{4-[2-（5-methyl-2-phenyloxazol-4-yl）ethoxy]phenyl}propanoic Acids

The synthesis of （S）-2-（3-arylacrylamido）-3-{4-[2-（5-methyl-2-phenyloxazol-4-yl）etho- xy]phenyl}propanoic acids is described. Their structures were confirmed by ^1H-NMR.     

Synthesis,Characterization, and Molecular Docking Study of N-[4-(1H-Benzimidazol-2-yl)-1,3-thiazol-2-yl]-1-[(E)-phenyldiazenyl)-1-phenylmethanimines

Russian Journal of Organic Chemistry - A series of new benzamidine derivatives have been synthesized in good yields by involving 1-(1H-benzimidazol-2-yl)-2-bromoethanone,...     

Synthesis of isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]nitrobenzenes by nitration of the corresponding isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]benzenes

Isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]nitro(dinitro)benzenes were synthe-sized in high yields by nitration of the corresponding 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]benzenes with a mixture of 100% nitric acid and concentrated sulfuric acid. The influence of 3- and 4-nitrofuroxanyl fragments on the regioselectivity of the nitration was revealed. The structure of 1,3-bis(4-nitrofuroxan-3-yl)-4-nitrobenzene was confirmed by X-ray diffraction analysis. 1,3- and 1,4-Bis(3-nitrofuroxan-4-yl)nitrobenzenes underwent thermal isomerization to more thermodynamically favorable 1,3- and 1,4-bis(4-nitrofuroxan-3-yl)nitrobenzenes.     

Design,Synthesis, and Anticancer Evaluation of N-(4-{5-[4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenyl]-4-(2,3,4-trimethoxyphenyl)-1,3-thiazol-2-yl}phenyl)benzamides

Russian Journal of Organic Chemistry - A series of substituted N-(4-{5-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-4-(2,3,4-trimethoxy­phenyl)-1,3-thiazol-2-yl}phenyl)benzamides were designed...