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1.
Sobhi M. Gomha 《Monatshefte für Chemie / Chemical Monthly》2009,140(2):213-220
Abstract The reaction of 2-mercapto-6,7,8,9-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one or its 2-methylthio derivative with hydrazonoyl halides, in the presence of triethylamine, yielded 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones. The structure of the latter compounds was further confirmed by reaction of 2-mercapto-6,7,8,9-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one with the appropriate active chloromethylenes followed by coupling of the products with benzenediazonium chloride
to afford the non-isolable azo-coupling products which converted, in situ, to 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones. The reaction mechanism was proposed and the products were screened for their biological activity. Some
of the newly synthesized compounds had a moderate effect against some bacterial and fungal species.
Graphical abstract
相似文献
2.
新型环烷烯并嘧啶并噻唑-3-酮类化合物的合成 总被引:1,自引:0,他引:1
以环戊酮、环庚酮为起始原料合成的环烷烯并[1,2-d]嘧啶-2-硫酮(2)与氯乙酸、芳香醛反应, 合成具有潜在抗癌活性的稠合杂环化合物5-芳基-2,8-二芳亚甲基-2,3,6,7-四氢-5H,8H-环戊烯并[1,2-d]噻唑并[3,2-a]嘧啶-3-酮(3)以及5-芳基-2,10-二芳亚甲基-2,3,6,7,8,9-六氢-5H,10H-环庚烯并[1,2-d]噻唑并[3,2-a]嘧啶-3-酮(4). 3和4的结构经1H NMR, IR, MS分析确认. 相似文献
3.
B. Zh. Elmuradov Kh. A. Bozorov Kh. M. Shakhidoyatov 《Chemistry of Heterocyclic Compounds》2011,46(11):1393-1399
2,3-Dimethyl- and 2,3-tri-, 2,3-tetra-, and 2,3-pentamethylene-substituted 8-arylidene-6,7-dihydro-pyrrolo[1,2-a]thieno[2,3-d]pyrimidin-4-ones were synthesized by the reaction of 2,3-dimethyl- and 2,3-tri-, 2,3-tetra-, and 2,3-pentamethylene-7,8-dihydropyrrolo[1,2-a]thieno[2,3-d]pyrimidin-4(6H)-ones with benzaldehyde, its 4-dimethylamino-, 3,4-dimethoxy-, and 3,4-methylenedioxy derivatives and also
furfural in the presence of NaOH. 相似文献
4.
E. A. Sidorova E. S. Kostenko I. S. Arustamova E. A. Kaigorodova L. D. Konyushkin 《Chemistry of Heterocyclic Compounds》2011,47(3):294-301
The reactions of 2-aminonicotinamides with triethyl orthoformate, carboxylic acids chlorides, aldehydes, and 2-formylbenzoic
acid were studied. As a result pyrido[2,3-d]pyrimidin-4(1H)-ones, 2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-ones, and 5,7,11b,12-tetrahydropyrido[2',3':4,5]pyrimido- [2,1-a]isoindole-5,7-diones were obtained. 相似文献
5.
The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with hydrazine to give selectively 6-amino-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones 5. Compounds 5 were further transformed to iminophosphoranes 6 by reaction with triphenylphosphine, hexachloroethane and triethylamine. A tandem aza-Wittig reaction of iminophosphorane 6 with isocyanate or acyl chloride generated previously unreported 3,5-dihydro-1,2,3-triazolo[4,5-d]-1,2,4-triazolo[1,5-a]pyrimidin-9-ones 10 or 12 in satisfactory yield. X-ray structure analysis of 10 g verified the proposed structure and the reaction selectivity. 相似文献
6.
Yvonne Syha Charlene Valmalle Jan W. Bats Michael Kock Mona Abdel-Tawab Manfred Schubert-Zsilavecz 《Monatshefte für Chemie / Chemical Monthly》2006,58(2):1357-1364
Although various thiazoles are known in literature for their biological and pharmacological properties only a few multi-step
synthesis pathways for the preparation of thiazolo[3,2-a]pyrimidinones have been reported, which are tedious and time-consuming. An alternative synthesis pathway is described, which
allows the preparation of 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones in a one-step process based on a Michael-type tandem reaction. By heating of 2-thiobarbituric acid with ethyl 4-bromocrotonate in ethanol at 60°C for 2 h, a 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one was obtained in 73% yield, whereas carrying out the reaction at room temperature results in the formation
of an unstable unsaturated ester. The structures of both, the α,β-unsaturated ester as well as the 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one were confirmed by NMR spectroscopy. Additionally, the structure of the 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one was investigated by single-crystal X-ray analysis. The described approach offers a significant improvement
over previously reported synthesis pathways because it allows the simple preparation of 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones with good yields in a one-step reaction. 相似文献
7.
8.
以2-溴丙酸甲酯、α,α-二氯甲基甲醚和胍唑为原料, 经缩合以及环化反应制得2-氨基-6-甲基-5-氧代-4,5-二氢-1,2,4-三氮唑并[1,5-a]嘧啶. 为了提高其在有机溶剂中的溶解性, 该化合物再同1-溴丁烷发生亲核取代反应得到了2-氨基-6-甲基-5-氧代-4-正丁基-4,5-二氢-1,2,4-三氮唑并[1,5-a]嘧啶, 然后与芳基醛和叔丁基异氰发生Ugi多组分反应, 合成了一系列具有潜在催吐活性的2-取代氨基-6-甲基-5-氧代-4-正丁基-4,5-二氢-1,2,4-三氮唑并[1,5-a]嘧啶类衍生物, 产品结构经质谱、核磁共振谱及元素分析确认. 相似文献
9.
A. Monge Vega I. Aldana M. M. Rabbani E. Fernandez-Alvarez 《Journal of heterocyclic chemistry》1980,17(1):77-80
This paper describes the synthesis of the previously unknown 11H-1,2,4-triazolo[4,3-b]pyridazino[4,5-b]indoles (2) and 11H-tetrazolo[4,5-b]pyridazino[4,5-b]indoles (3) from 4-hydrazino-5H-pyridazino[4,5-b]indoles (1) , as well as the synthesis of 1,2,4-triazolo[3,4-f]-1,2,4-triazino-[4,5-a]indoles (10) from 2-indolecarbohydrazide (4) . Compounds 2 were obtained by acylation of compounds 1 , followed of thermal cyclization and compounds 3 by treating compounds 1 with nitrous acid. The reactions of compound 4 with formic acid or ethyl orthoformiate gave 1,2-dihydro-1-oxo-1,2,4-triazino[4,5-a]indole (6) . Treating this last compound with phosphorus oxychloride or phosphorus pentasulfide, followed by hydrazine, gave 1-hydrazino-1,2,4-triazino-[4,5-a]indole (9) . Acylation of this last compound, followed of cyclization gave compounds 10 . All the compounds were characterized by elemental analysis and ir and 1H-nmr spectra. 相似文献
10.
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. 相似文献
11.
A. V. Bentya R. I. Vas’kevich A. V. Turov E. B. Rusanov M. V. Vovk V. I. Staninets 《Russian Journal of Organic Chemistry》2011,47(7):1066-1073
6-Allyl(diallyl, prop-2-yn-1-yl)amino-1-R-pyrazolo[3,4-d]pyrimidin-4(5H)-ones reacted with iodine to give angularly fused 8-iodomethyl-7,8-dihydro-1-R-imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-ones which were treated with sodium acetate to obtain 8-methylidene-1-R-7,8-dihydroimidazo[1,2-a]pyrazolo-[4,3-e]pyrimidin-4(6H)-ones as a result of elimination of hydrogen iodide. 8-Methylidene-1-R-7,8-dihydroimidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-ones were converted into 8-methyl-1-R-imidazo[1,2-a]pyrazolo-[4,3-e]pyrimidin-4(5H)-ones on heating to the melting point. 8-Methylidene-1-phenyl-7,8-dihydroimidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-one underwent isomerization into linearly fused 6-methyl-1-phenyl-1,8-dihydro-4H-imidazo[1,2-a]pyrazolo[3,4-d]pyrimidin-4-one on heating in sulfuric acid. 相似文献
12.
L. M. Mironovich M. A. Ivanov E. P. Koval'chuk 《Chemistry of Heterocyclic Compounds》2001,37(9):1150-1152
8-tert-Butyl-9-oxo-1,2,4-triazolo[4,5-b]-1,2,4-triazolo[3,4-c]-1,2,4-triazine has been synthesized by the interaction of 6-tert-butyl-3-hydrazino-1,2,4-triazolo[3,4-c]-1,2,4-triazin-5-one with formic acid. The conditions of carrying out the reaction are discussed. Spectral characteristics are given. 相似文献
13.
2-Hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one 2a and 7-hydroxy-5H-thiazolo[3,2-a]pyrimidin-5-one 2b, were obtained in high yields under mild conditions from the cyclization reactions of bis-(2,4,6-trichlorophenyl) malonate and 2-aminobenzothiazole or 2-aminothiazole, respectively. A new class of compounds, 2,3-dihydro-4H-benzo[4,5]thiazolo[3,2-a]furo[2,3-d]pyrimidin-4-ones and 6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones, were synthesized via the microwave assisted radical addition of compounds 2a and 2b to various alkenes using manganese(III) acetate. A preliminary acetylcholine esterase (AchE) inhibition test of compound 4e showed excellent (92%) inhibitory potential, comparable with the standard drug Donapezil®. 相似文献
14.
15.
5‐Substituted 7H‐1,2,3‐triazolo[4,5‐d]pyrimidin‐7‐ones ( 4 ) were rapidly prepared by a solution‐phase parallel synthetic method, which includes aza‐Wittig reaction of iminophosphorane ( 1 ) with phenyl isocynate to give carbodiimide ( 2 ) and subsequent reaction of 2 with various amine and alcohols in the presence of catalytic amount of sodium alkoxide in a parallel fashion. 相似文献
16.
Yehia A. Ibrahim S. A. L. Abdel-Hady M. A. Badawy M. A. H. Ghazala 《Journal of heterocyclic chemistry》1982,19(4):913-915
3-Methylmercapto-5-oxo-6-vinyl- and 2-methyl-3-mercapto-5-oxo-6-vinyl-2,5-dihydro-1,2,4-triazines were readily converted into the corresponding thieno[2,3-e]-1,2,4-triazine in one step by the action of phosphorus pentasulfide in pyridine. 4-Methyl-3-mercapto-5-oxo-4,5-dihydro-1,2,4-triazine is only converted into the 5-thioxo analog and no thiophene ring product was obtained under the same conditions. Thieno[2,3-e]-1,2,4-triazines were also more efficiently obtained by the action of phosphorus petnasulfide in pyridine on the appropriate 6-acylmethyl-3-mercapto-5-oxo-2,5-dihydro-1,2,4-triazine. 相似文献
17.
A novel solid-phase method for the synthesis of 4-methyl-pyrido[2,3-d]pyrimidin-7-one compounds with two diversity points is described. The polymer supported methylsulfonyl derivatives A3, achieved by coupling compound G with different resin-bound amines A1 followed by oxidation with MCPBA, are substituted with several amines R1R2NH. Final cleavage affords 126 compounds having formula H in good yield and purity. 相似文献
18.
Mohammad Rahimizadeh Mehdi Pordel Mehdi Bakavoli Zahra Bakhtiarpoor Ala Orafaie 《Monatshefte für Chemie / Chemical Monthly》2009,20(2):633-638
Abstract
New imidazo[4,5-a]acridone derivatives were synthesized from the rearrangement of 3H-imidazo[4′,5′:3,4]benzo[c]isoxazoles. New imidazo[4,5-a]acridines were obtained from the reaction of imidazo[4,5-a]acridones in boiling POCl3. All of these compounds exhibited antimicrobial activities comparable to streptomycin as reference drug. 相似文献19.
The synthesis of 1,2,4-triazolo[4,3-b]pyridazines and the unknown ring system, pyrazino[2,3-d]-1,2,4-triazolo[4,3-b]pyridazine, has been achieved. The preparation of the new tricyclic 1,2,4-triazole was accomplished first by ring closure of the triazole ring followed by formation of the pyrazine ring. Substitution of the pyrazino[2,3-d]-1,2,4-triazolo[4,3-b]pyridazine ring system was carried out in order to provide information of its reactivity and to provide a variety of interesting compounds for biological testing. 相似文献
20.
Jiri KasparecJerry L. Adams Joseph SiskoDomingos J. Silva 《Tetrahedron letters》2003,44(24):4567-4570
A novel, highly efficient and scalable route for the synthesis of trisubstituted pyrido[2,3-d]pyrimidin-7-ones was developed. The target compounds were synthesized in five steps from readily available reagents in about 40% overall yield. 相似文献