Zn(OAc)2 catalyzed microwave irradiated synthesis of substituted thieno[2,3-d]pyrimidin-4(3H)-one

Different Lewis acids were screened to catalyze the reaction of 2-amino-thiophene-3-carboxylate, orthoformate and aryl amine to form 2-substituted thieno[2,3-d]pyrimidin-4(3H)-one. Zn(OAc)₂ was demonstrated to efficiently catalyze the reaction. 20 substituted thieno[2,3-d]pyrimidines were synthesized by adding 0.5% mol Zn(OAc)₂ as catalyst under microwave irradiation.     

选择性合成双[噻吩并[2,3-d]嘧啶-4(3H)-酮]

以2-氨基-4-三氟甲基-5-甲基-噻吩-3-羧酸乙酯(1)为起始原料制得膦亚胺2.在碳酸钾的催化下,膦亚胺2与芳基异氰酸酯和伯二胺的氮杂Wittig反应制得嘧啶环上2,2’取代的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]3;膦亚胺2与烷基异氰酸酯和伯二胺的氮杂Wittig反应制得嘧啶环上3,3’取代的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]4.化合物3的核磁共振氢谱表明关环反应在嘧啶环的2,2’位;化合物4的核磁共振氢谱表明关环反应在嘧啶环的3,3’位.对合成反应机理的推导及目标产物核磁共振氢谱数据的分析解释了此合成反应的选择性.     

Microwave-assisted synthesis of new pyrimido[4′,5′：4,5]thiazolo[3,2-α] benzimidazol-4（3H）-one derivatives in solvent-free condition

Microwave-assisted synthesis of new 2-arylpyrimido[4′,5′：4,5]thiazolo[3,2-α]benzimidazol-4（3H）-ones from 3-aminothia- zolo[3,2-α]benzimidazol-2-earboxamide and aroyl halides in solvent-free condition is described. In comparison with classical conditions the reactions are faster and the yields are higher under microwave irradiation.     

桥连的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]的合成

2-氨基-4-三氟甲基-5-甲基-噻吩-3-羧酸乙酯(1)与三苯基膦、六氯乙烷及三乙胺反应,以84％的产率得到膦亚胺2.在碳酸钾的催化下,膦业胺2与芳基异氰酸酯和双官能亲核试剂的串联氮杂Wittig反应制得新型桥连的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]3,产率为58％～82％.所有产物结构经IR,1HNMR,MS表征和元素分析确证.     

Synthesis of pyrido[2,3-d]pyrimidin-4-one derivatives

This paper describes one-pot synthesis of 5H-[1,3]thiazolo[3,2-a]pyrido[3,2-e]pyrimidin-5-one 4 , 5H-dipyri-do[1,2-a:3′,2′-e]pyrimidin-5-one 10 and 5H-pyrido[3,2-e]pyrimido[1,2-a]pyrimidin-5-one 15 and some of their derivatives, starting with 2-chloro-3-pyridine carboxilic acid 1. Compounds 4 and 10 reacted with phosphorus pentasulfide to give the respective 5-thione analogues, 5 from 4 and 11 from 10 . Boiling the 5-thione derivatives with hydrazine hydrate, the respective 5-hydrazono derivatives 6 from 5 and 12 from 11 were obtained. The 5-acetyl hydrazono, 7 , and the 5-isopropylidenehydrazono, 8 , derivatives were also prepared from 6 , and the 5-propionylhydrazono derivatives, 13 , from 12 . Compound 4 reacted with hydrazine to give an adduct with two molecules of hydrazine and the probable structure 16 . Treating this adduct with acetone a monohydrazone 17 was obtained. Boiling a suspension of this adduct in DMF, it gave 6,10-dihydro-6H-pyrido[3′,2′:5,6]pyrimido[2,1-c][1,2,4]triazin-5-one 20 .     

Efficient Synthesis,Crystal Structure and Antibacterial Activity of Two Novel Thieno [2,3-d] pyrimidin-4(3H)-one Derivatives

Two new thieno[2,3-d]pyrimidin-4(3H)-one derivatives,C24H22 Cl N3O2S(5a) and C25H25N3O2S(5b),have been synthesized via a tandem aza-Wittig reaction.This tandem reaction has many attractive aspects such as easily accessible and versatile starting materials,mild conditions and high yields.Both compounds have been characterized by elemental analysis,HR-MS,IR,NMR spectra and X-ray single-crystal diffraction.Compound 5a crystallizes in monoclinic,space group P21/c with a = 9.986(3),b = 14.263(4),c = 15.530(5)?,β = 93.806(5)o,V = 2207.1(11) ?3,Mr = 451.96,Z = 4,Dc = 1.360 g/cm3,F(000) = 944,μ = 0.294 mm-1,Mo Kα radiation(λ = 0.71073 ?),the final R = 0.0444 and w R = 0.1219 for 3407 observed reflections with I 2σ(I).Compound 5bcrystallizes in triclinic,space group P1 with a = 8.974(4),b = 10.766(5),c = 12.260(6) ?,β = 93.047(7)o,V = 1122.1(9) ?3,Mr = 431.54,Z = 2,Dc = 1.277 g/cm3,F(000) = 456,μ = 0.170 mm-1,Mo Kα radiation(λ = 0.71073 ?),the final R = 0.0378 and w R = 0.1072 for 3806 observed reflections with I 2σ(I).The preliminary antibacterial activities of 5a and 5b were investigated.Compound 5a showed 71.3% and 79.2% in vitro inhibition against Fusarium oxysporium and Rhizoctonia solani,respectively.Compound 5b showed 75.3% in vitro inhibition against Rhizoctonia solani.     

An efficient route for synthesis of 2-alkylamino benzo[b]thieno[3,2-d]pyrimidin-4(3H)-one

The carbodiimide 2,obtained from the aza-Wittig reactions of iminophosphorane 1 with alkyl isocyanates,reacted with primary amino to give 2-alkylamino benzo[b]thieno[3,2-d]pyrimidin-4(3H)-ones 4 and 5.The formation mechanism of the title compounds has been investigated.     

Synthesis and Crystal Structure of 2-Ethoxy-3-n-butyl-benzofuro[2,3-d]pyrimidin-4（3H）-one

The crystal structure of the new title compound 2-ethoxy-3-n-butyl- benzofuro[2,3d]pyrimidin-4（3H）-one （C16H18N2O3, Mr = 286.32） has been prepared and determined by singlecrystal X-ray diffraction. The crystal is of monoclinic, space group P21/c with a = 13.7167（14）, b = 13.113（1）, c = 8.378（1） A, β = 98.992（2）^o, V = 1488.4（3） A^3, Z = 4, Dc = 1.278, F（000） = 608, μ = 0.089 mm^-1, MoKa radiation （2 = 0.71073）, R = 0.0498, wR = 0.1238 for 2336 observed reflections with I 〉 2σ（I）. X-ray diffraction analysis reveals that all ring atoms in the benzo[4, 5]furo [2,3-d] pyrimi- dinone moieties are almost coplanar.     

Microwave synthesis,characterization and antimicrobial study of new pyrazolyl-oxopropyl-quinazolin-4(3H)-one derivatives

Heterocyclic compounds containing pyrazolyl-oxopropyl-quinazolin-4(3H)-one are reported to possess significant biological activity. Syntheses of 6-bromo-2-(3-chloro-2-oxopropyl)-3-(4-fluorophenyl)quinazolin-4(3H)-one 2 6-bromo-3-(4-fluorophenyl)-2-(3-hydrazinyl-2-oxopropyl)quinazolin-4(3H)-one 3 and 6-bromo-2-(3-(3-(4-(1-(2-chlorophenyl)-3-methyl-1H-pyrazol-5(4H)-ylideneamino)phenyl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxopropyl)-3-(4-fluorophenyl)quinazolin-4(3H)-one 5a–j using microwave irradiation have been described. These compounds have been characterized on the basis of the UV, IR, ¹H NMR, ¹³C NMR, Mass and elemental analysis. Compounds have been evaluated for their antimicrobial activity.     

5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4(3H)-酮类查尔酮的设计、合成及体外抗肿瘤活性

以环己酮、氰乙酸乙酯、硫粉和吗啉为原料,依次通过Gewald反应、关环反应、Chan-Lam偶联反应和Claisen-Schmidt缩合反应以23.9%-40.9%的总收率合成了18个新型5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4(3H)-酮类查尔酮化合物,所有化合物结构经过了¹H NMR和MS的确证。初步的生物活性测试表明,目标化合物对乳腺癌MCF-7和MDA-MB-231细胞均显示出抑制活性。      

A facile one-pot synthesis of new thieno- [2,3-d]pyrimidine-2,4（1H,3H）-dione derivatives

A facile one-pot synthesis of new 3-arylthieno[2,3-d]pyrimidine-2,4(1H,3H)-diones via base-catalyzed cyclocondensation of ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate with aryi isocyanates is described.     

Derivatives of condensed thieno[2,3-d]-pyrimidines. 20. Synthesis of 2-substituted 5,6-dihydro-8H-pyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-ones and 5,6,7,8-tetrahydrobenzo-[b]thieno[2,3-d]pyrimidin-4-ones

We have developed a method for obtaining 2-substituted 3-amino-6,6-dimethyl-5,6-dihydro-8H-pyrano[4′,3′:4,5]-and 5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4(3H)-ones, converted by deamination to the corresponding dihydropyranothieno-3H-pyrimidinones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 441–444, March, 2006.     

Nitriles in heterocyclic synthesis: A novel synthesis of some thieno[2,3-d]pyrimidine and thieno[2,3-b]pyridine derivatives

A simple route to the synthesis of the pharmaceutically important thieno[2,3-d]pyrimidine derivatives and of thieno[2,3-b]pyridine derivatives via the use of 5-amino-3-phenylthiophene-2,4-dicarbonitrile (2) as a starting material is described. © 1996 John Wiley & Sons, Inc.     

Facile synthesis of novel fluorinated thieno[2,3-d]pyrimidine derivatives containing 1,3,4-thiadiazole

A series of novel fluorinated thieno[2,3-d]pyrimidine derivatives incorporating 1,3,4-thiadiazole were synthesized by a facile microwave-assisted procedure,including the cyclization of 2-aminothiophene-3-carbonitrile with trifluoroacetic acid,chlorination and nucleophilic substitution reaction.This protocol offered such advantages as mild reaction conditions,short reaction time, simple puritication and good yields.The structures of the products were characterized by ~1H NMR,MS,elemental analysis and Xray diffraction.     

A rapid synthesis of isoxazolo[5,4-d]pyrimidin-4（5H）-ones under microwave irradiation with solid acid catalysis in solvent-free conditions

A rapid and efficient method for the synthesis of isoxazolo[5,4-d]pyrimidin-4（5H）-ones has been developed through cyclocondensation of 5-aminoisoxazole-4-carboxamides with orthoesters under conventional heating and solvent-free microwave irradiation with solid acid catalysis. In comparison, the reactions are faster and the yields are higher under microwave irradiation.     

Synthesis of condensed derivatives of 2-substituted thieno[2,3-d]pyrimidin-4-ones

A preparative method of synthesis of 2-substituted thieno[2,3-d]pyrimidin-4-ones involving deamination of the corresponding 3-amino derivatives, by sodium nitrite in acidic medium is proposed. A possible reaction mechanism is considered.A. L. Mndzhoyan Institute of Fine Organic Chemistry. Academy of Sciences of the Republic of Armenia, Erevan 375014 Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 941–944, July, 1999.     

Synthesis of 5-glycopyranosylamino-pyrano[2,3-d]pyrimidin-2-one derivatives

Summary Three series of 3-substituted 5-glycopyranosylamino pyrano[2,3-d]pyrimidin-2-one derivatives,3 a–c,4 a–c, and5 a–c have been prepared by treatment of the corresponding 1,4-dihydro-6-glycopyranosylamino pyrimidin-4-ones1 a–c with malonic, methyl malonic and ethyl malonic acids, respectively.

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Synthese von Derivaten des 5-Glucopyranosylaminopyrano[2,3-d]pyrimidin-2-on

Zusammenfassung Es wurden drei Serien von 3-substituierten 5-Glucopyranosylaminopyrano[2,3-d]pyrimidin-2-onen (3 a–c,4 a–c und5 a–c) mittels Behandlung der entsprechenden 1,4-Dihydro-6-glucopyranosylamino-pyrimidin-4-one (1 a–c) mit Malon-, Methylmalon- bzw. Ethylmalonsäure dargestellt.

     

新型2-氨基-呋喃并[2,3-d]嘧啶-4(3H)-酮衍生物的合成及抗肿瘤活性

报道应用aza-Wittig反应,采用易得的原料,在温和的条件下,以78%～90%的产率有效的合成了新型2-氨基-呋喃并[3,2-d]嘧啶-4(3H)-酮衍生物5,其结构经IR,1H NMR,MS和元素分析确认.为进一步得到结构确认,化合物5c经X射线衍射分析证实.运用噻唑蓝(MTT)标准法对化合物5进行了体外抗肿瘤活性的测定,其中5f对肺癌细胞A459的IC50值为18.4μmol/L,显示出潜在良好的抗肿瘤活性.     

A new route to the synthesis of 4-amino-substituted pyrido[2,3-d]pyrimidin-5-one derivatives

The reaction of 6-(R-amino)-5-acetyl-4-methylsulfonyl-2-phenylpyrimidines with amines was studied. 6-Arylamino derivatives react with alkylamines to form 6-alkylamino-4-arylamino-5-acetyl-2-phenylpyrimidines, which upon refluxing in benzene with dimethylformamide dimethylacetal are converted to 4-alkylamino-8-aryl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-ones. The cyclization proceeds selectively with participation of the arylamino group only, the alkylamino group being not involved. At the same time, refluxing of 5-acetyl-4,6-dibenzylamino-2-phenylpyrimidine with dimethylformamide dimethylacetal in toluene affords the product of condensation on the acetyl group, which upon refluxing in o-xylene transforms to 4-benzylamino-8-benzyl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-one.