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1.
《Journal of Sulfur Chemistry》2013,34(6):605-615
Derivatives containing the cyclohepta4′,5′thieno[2′,3′:4,5]pyrimido[1,2-b][1,2,4,5]-tetrazin-6-one system were prepared from the reaction of 3-amino-2-thioxo-1,2,3,5,6,7,8,9-octahydro-4H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-one (5) or its 2-methylthio derivative 6 with hydrazonoyl chlorides 9. The mechanism of the studied reactions has been discussed and the biological activity of the isolated products has been evaluated. 相似文献
2.
《Journal of Sulfur Chemistry》2013,34(6):630-636
A simple original approach to earlier unknown parent 2,7-dihydrothiopyrano[2,3-b]pyrrole (5) from allyl isothiocyanate and propargyl bromide via one-pot synthesis and thermal rearrangement of 2-(prop-2-ynylsulfanyl)-1H-pyrrole (4) has been developed. The compound 5 in the present study was successfully examined as 2,7-dihydrothiopyrano[2,3-b]pyrrole scaffold in the synthesis of corresponding N- and C-pyrrolecarbodithioates. 相似文献
3.
《Journal of Sulfur Chemistry》2013,34(3):275-284
A series of some new fused thiopyrano[2,3-d]thiazole derivatives have been synthesized by a stereo-selective hetero-Diels-Alder reaction of 5-(2,4-dihydroxy-benzylidene)-4-thioxo-thiazolidine derivatives 3a,b with acrylonitrile, ethyl acrylate, N-phenylmale-imide, ω-nitrostyrene and N-phenyl-1, 3, 4-triazole-2,5-dione. 5-Amino-9-hydroxy-dihydro-benzopyrano[3′,4′:4,5]thiopyrano[2,3-d]thiazol-6-one derivatives 14a,b have been synthesized by Michael addition of 3a,b with malononitrile. Structures and conceivable mechanisms are discussed. 相似文献
4.
A series of novel thieno[2,3-b]pyridines were prepared from the reaction of the appropriate bromoacetylbenzofurans or bromoacetylbenzothiazole with the corresponding pyridinethione derivatives in ethanolic sodium ethoxide at reflux. Moreover, new bis(thieno[2,3-b]pyridine) derivatives have also been synthesized by the reaction of the appropriate bis-bromoacetyl derivatives with the corresponding pyridinethiones in the presence of sodium ethoxide. Attempts to synthesize the target bis(thieno[2,3-b]pyridine) derivatives by bis-alkylation of the corresponding (thieno[2,3-b]pyridin-2-yl)(hydroxyphenyl)methanone with the appropriate dihaloalkanes using a mild base were unsuccessful. 相似文献
5.
An efficient microwave-assisted synthesis of thieno[2,3- b ]quinolines under solvent-free conditions
《Journal of Sulfur Chemistry》2013,34(4-5):373-379
A novel and efficient method for the synthesis of substituted thieno[2,3-b]quinolines has been developed. A simple one-pot reaction of 3-formyl-2-mercaptoquinolines 2a–l with 1-chloroacetone, 2-chloroacetamide, ethyl chloroacetate and 2-chloro-1-phenylethanone in presence of catalytic amount of potassium carbonate under microwave irradiation and solvent-free conditions gave thieno[2,3-b]quinolin-2-ylethanone derivatives 3a–e, thieno[2,3-b]quinoline-2-carboxamide derivatives 4a–e, ethyl thieno[2,3-b]quinoline-2-carboxylate 5a–e and phenyl(thieno[2,3-b]quinolin-2-yl)methanone derivatives 6a–e compounds respectively. The structures of all the newly synthesised compounds were elucidated on the basis of elemental analysis, IR, 1H NMR and mass spectral data. 相似文献
6.
《Journal of Sulfur Chemistry》2013,34(4-5):405-410
Pyrimido[1,2-b][1,2,4,5]tetrazin-6-one, tetrazino[3,2-b]quinazolin-5-one, pyrimidino[1,2-b]1,2,4,5-tetrazin-5-one and triazolo[4,3-a]pyrimidine derivatives were synthesized from C-(4-methyl-2-phenyl)thiazol-5-oyl-N-phenyl-hydrazonoyl bromide and different pyrimidine-2-thiones. New compounds had their structures confirmed by elemental and spectral analysis and were screened antimicrobial activity. 相似文献
7.
Mitsuo Miyazawa Masahiro Nobata Shigeaki Okamura Osamu Muraoka Genzoh Tanabe Hiromu Kameoka 《Journal of chemical technology and biotechnology (Oxford, Oxfordshire : 1986)》1998,71(4):281-284
The biotransformation of (±)-bicyclo[3.3.1]nonane-2,6-dione by Aspergillus niger and Glomerella cingulata was investigated. The diketone was reduced to the ketoalcohol 2-endo-hydroxy-bicyclo[3.3.1]nonane-6-one and the diol endo,endo-bicyclo[3.3.1]nonane-2,6-diol respectively. Endo,endo-bicyclo[3.3.1]nonane-2,6-diol and ketoalcohols produced by G. cingulata had high optical purity, on the other hand, reduction by A. niger yielded optically active (-)-(1R, 2S, 5R, 6S)-bicyclo[3.3.1]nonane-2,6-diol(99·9% e.e.). © 1998 SCI 相似文献
8.
Michail N. Elinson Alexey I. Ilovaisky Valentina M. Merkulova Dmitry V. Demchuk Pavel A. Belyakov Yuri N. Ogibin Gennady I. Nikishin 《Electrochimica acta》2008,53(28):8346-8350
Electrochemically induced catalytic multicomponent transformation of isatins, barbituric acid or N-alkyl barbiturates and malononitrile in alcohols in an undivided cell results in the formation of substituted 7′-amino-2,2′,4′-trioxo-1,1′,2,2′,3′,4′-hexahydrospiro[indole-3,5′-pyrano[2,3-d]pyrimidine]-6′-carbonitriles in 80–95% yields. The developed efficient electrocatalytic approach to corresponding spiro[indole-3,5′-pyrano[2,3-d]pyrimidine] system is beneficial from the viewpoint of diversity-oriented large-scale processes and represents a new example of the ecologically pure synthetic concept for electrocatalytic multicomponent reactions strategy. 相似文献
9.
Prof. Andrew Tsotinis Dr. Pandelis A. Afroudakis Prof. Ioannis P. Papanastasiou Aikaterini Sakellaropoulou Marina Boniakou Prof. Dimitri Komiotis Prof. Peter J. Garratt Dr. Philippe Delagrange Dr. Alina Bocianowska-Zbrog Prof. David Sugden 《ChemMedChem》2022,17(12):e202200129
A series of substituted indolo[2,1-a]isoquinolines and indolo[1,2-a]benzoxazines have been prepared, as melatonin analogues, to investigate the nature of the binding site of the melatonin receptor. Agonist and antagonist potency of all the analogues was measured using the [35S]GTPγS binding assay protocol. The binding affinity of the analogues were measured by competition binding studies against the human MT1 (hMT1) and MT2 (hMT2) receptors stably transfected in Chinese Hamster Ovarian (CHO) cells, using 2-[125I]-iodomelatonin, as a ligand. N-Acetyl 2-(10-methoxy-5,6-dihydroindolo[2,1-a]isoquinolin-12-yl)propyl-1-amine (12 a) binds strongly to both the hMT1 and hMT2 receptors, and shows a preference for the hMT2, as does its propanamido counterpart 12 b . The introduction of two methyl groups into their side chain, analogues 15 a and 1 5 b , leads to antagonism, in the case of the former, and drastically diminishes its hMT1 binding; an analogous profile is seen for 15 b , which, however, is a partial agonist. Introduction of chlorine or methoxy groups into ring 4 gives compounds, that are weakly binding, with a preference for MT2. Substitution of oxygen for carbon at position 5 gives the indolo[1,2-c]benzoxazines 33 , 36 a and b , that bind strongly to the human receptors, 33 , 36 b being potent agonists at the melatonin receptors, but do not discriminate between hMT1 and hMT2. 相似文献
10.
《Journal of Sulfur Chemistry》2013,34(4-5):381-391
Pyridine-2(1H)-thione 1 reacted with phenyl isothiocyanate to give pyrido[2,3-d]pyrimidine derivative 3. Compound 3 reacted with halogen containing compounds 4a–d and methyl iodide in dimethylformamide/potassium hydroxide solution at room temperature to give 2,7-bisalkylthiopyrido[2,3-b]pyrimidine derivatives 5a–d and 9, respectively. Compounds 5a–d could be cyclized into thienopyrido[2,3-d]pyrimidine derivatives 6a–d by boiling with ethanolic potassium hydroxide solution. Compound 6a reacted with acetic anhydride or formic acid and gave the corresponding pyrimido[4″,5″:4′,5′]thieno[3′,2′:5,6]pyrido[2,3-d]pyrimidine derivatives 8a,b. Compound 9 reacted with hydrazine hydrate to yield pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine derivative 11 which could be reacted with nitrous acid and dimethylformamide-dimethylacetal (DMF-DMA) and gave the final isolable products corresponding to the pyrazolo[4′,3′:5,6]pyrido[2,3-d]tetrazolo-[5,1-b]pyrimidine and pyrimido[1″,2″:1′,5′]pyrazolo[4′,3′:5,6]pyrido[2,3-d]1 2 4triazolo-[4,3-b] pyrimidine derivatives 13 and 17, respectively. Compound 11 also reacted with some β-dicarbonyl compounds such as acetylacetone (18) and ethyl acetoacetate (20) to yield the corresponding pyrimido[1″,2″:1′,5′]pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine derivatives 19 and 21, respectively. Finally, compound 11 reacted with chloroacetyl chloride (22) to give the corresponding imidazo[1″′,2″′:1″,5″]pyrazolo[4″,3″:5′,6′]pyrido[3′,2′:5,6]pyrimido[2,1-c]1 2 4triazine derivative 23. 相似文献
11.
《Journal of Sulfur Chemistry》2013,34(1):49-55
The chemistry of imino-1,2,3-dithiazoles possessing a thiophene ring with various alkyl and aromatic diamines was investigated in the expectation of obtaining novel 2,3-condensed thieno[2,3-d]pyrimidinone derivatives. Obtained via Appel's salt's (1) chemistry, methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2-thiophenecarboxylate (2) is confirmed as a very interesting starting material for access to a variety of novel thiophene bioisosters of bioactive pentacyclic tetraaza-pentaphene-5, 8-diones. 相似文献
12.
《Journal of Sulfur Chemistry》2013,34(4):329-339
New functionalized pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one derivatives were synthesized via reaction of the hydrazonoyl halides with 7-(4-nitrophenyl)-5-phenyl-2,3-dihydro-2-thioxopyrido[2,3-d]pyrimidin-4(1H)-one or its 2-methylthio derivative. The biological activity of the products has been evaluated. The mechanism and the regioselectivity of the studied reactions have been discussed. 相似文献
13.
《Journal of Sulfur Chemistry》2013,34(2):170-177
Several 2-arylimidazo[2,1-b]benzothiazoles (4) have been conveniently synthesized in one-pot reactions via α-tosyloxylation of enolizable ketones (1) using [hydroxy(tosyloxy)iodo]benzene 2 in acetonitrile, followed by treatment with 2-amino-6-(substituted)benzothiazoles (3). The present protocol offers several advantages towards general access of 2-arylimidazo[2,1-b]benzothiazoles, including an intriguing alternative to the literature protocols, a readily available nontoxic reagent, operational simplicity and an environmentally benign procedure. 相似文献
14.
Abstract Syntheses of the fused heptacyclic polyarenes dibenzo[h,rst]pentaphene (1), naphthol[1,2,3,4-rst]pentaphene (2), and the pentacyclic polyarene 8H-naphth[1,2,3-de]anthracene (8), of interest in carcinogenesis research, are described. 相似文献
15.
《Journal of Sulfur Chemistry》2013,34(4):427-438
A new synthetic strategy for the synthesis of novel 6-methyl-3′-aryl spiro[isoxazolo[2,3-b][1,2,4]thiadiazole-2,2′-thiazolidin]-4′-ones (9a–9e) and 6-methyl-3′-aryl spiro[isoxazolo[2,3-b][1,2,4]oxadiazole- 2,2′-thiazolidin]-4′-ones (12a–12e) analogs is described. These compounds showed significant antimicrobial activity against all the standard strains. 相似文献
16.
《Journal of Sulfur Chemistry》2013,34(3):273-286
3-(4-Bromophenyl)-2-cyanoprop-2-enethioamide (1) reacted with ethyl 3-oxo-3-phenylpropanoate (2) to give ethyl 4-(4-bromophenyl)-5-cyano-2-phenyl-6-thioxo-1,6-dihydropyridine-3-carboxylate (3). Compound 3 was taken as a starting material for the synthesis of thio-substituted ethyl nicotinate derivatives 5a–d, which underwent cyclization to the corresponding thieno[2,3-b]pyridines 6a–d. Also 3 reacted with hydrazine hydrate to give the pyrazolo[3,4-b]pyridine derivative 7, which upon diazotization gave the diazonium derivative 8. Compound 6a condensed with dimethylformamide–dimethylacetal to afford thieno[2,3-b]pyridine derivative 9, which reacted with different amines 10a–e to afford the pyridothienopyrimidine derivatives 12a–e through the Dimroth rearrangement. Moreover, compound 6a reacted with different reagents to give pyridothienopyrimidine derivatives 14a and b, 17 and pyrazolothienopyridine derivative 18. In addition, acetylating compound 6c with chloroacetylchloride afforded the 3-[(2)-chloroacetylamino]thieno[2,3-b]pyridine derivative 20, which upon cyclization yielded the corresponding 2-chloromethylpyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine derivative 21. Some of the newly synthesized compounds were screened in vitro for their antimicrobial activities. 相似文献
17.
《Journal of Sulfur Chemistry》2013,34(5):329-342
1,3,4-Thiadiazolines, 1,3,4-selenadiazolines and triazolino[4,3-a]pyrimidines have been synthesized from 3-aza-[2,4-dimethyl(1,3-thiazol-5-yl)-2-bromo-3-substituted-amino]prop-2-en-1-ones with potassium thiocyanate, potassium selenocyanate, alkyl carbodithioates and 6-methyl-2-methylthio-4-substituted 3,4-dihydropyrimidine-5-carboxylates. Structures of the newly synthesized compounds have been established by elemental analysis, spectral data and alternative synthesis whenever possible. Some of products have been tested towards bacteria. 相似文献
18.
Abdolali Alizadeh Atefeh Roosta Kaveh Amir Ashjaee Asalemi 《Journal of Sulfur Chemistry》2018,39(4):435-442
An extremely concise one-pot procedure toward the synthesis of 2H-Thiopyrano [2,3-b]quinoline-2,3-dicarboxylates whose applications as medicines is predictable has been established. This approach produces three fused rings evolving from the formation of four new carbon–carbon bonds and a stereogenic center in a one-pot protocol. 相似文献
19.
《Journal of Sulfur Chemistry》2013,34(4):419-426
In presence of triethylamine, the reaction of substituted 2-aroyl-hydrazinecarbothioamides with 1,4-Diphenyl-but-2-yne-1,4-dione afforded novel furo[3,4-d]-1,3-thiazoles in good yield. The reaction mechanism suggests that the second molecule of 1,4-Diphenyl-but-2-yne-1,4-dione behaved as an oxidizing agent. 相似文献
20.
Zakaria K. Abd El-Samii Said A. El-Feky 《Journal of chemical technology and biotechnology (Oxford, Oxfordshire : 1986)》1995,63(2):135-140
The synthesis of several S- and N-substituted derivatives of 5-[(5,6-diphenyl-1,2,4-triazin-3-yl)oxymethyl]-s-triazole-3-thiol, 2-[(5,6-diphenyl-1,2,4-triazin-3-yl)-oxymethyl]-5,6-dihydrothiazolo-[3,2-b]-s-briazole, 2-[(5,6-diphenyl-1, 2,4-triazin-3-yl)oxymethyl]-5H,6,7-dihydro-s-triazolo-[3,2-b]-1,3-thiazine, 2-[(5,6-diphenyl-1,2,4-triazin-3-yl)oxymethyl]-5,6-dihydrothiazolo-[3,2-b]-s-triazol-5-one and 2-[(5,6-diphenyl-1,2,4-triazin-3-yl)oxymethyl]-6-phenylthiazolo-[3,2-b]-s-triazole is reported. All the novel compounds have been screened for antimicrobial activity and one of them showed noteworthy activity. 相似文献