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Al-Huniti MH El-Abadelah MM Zahra JA Sabri SS Ingendoh A 《Molecules (Basel, Switzerland)》2007,12(3):497-503
Model tetrahydropyrido[3',2':4,5]thieno[2,3-b][1,4]thiazines 9a-c were synthesized via reductive lactamization, using sodium dithionite, of the respective 2-[(carboxyalkyl)thio]-3-nitro-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acids 7a-c. The latter derivatives were made via interaction of 2-chloro-7-cyclopropyl-3-nitro-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid (6) with each of alpha-mercaptoacetic, alpha-mercaptopropionic, and alpha-mercaptosuccinic acids and triethylamine in aqueous acetone at room temperature. The structures of 7a-7c and 9a-9c are supported by microanalytical and spectral (IR, MS, NMR) data. Compounds 9a and 9c showed potent inhibitory activity against the IGROV1 (Ovarian Cancer) cell line. 相似文献
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William B. Wright George O. Morton Andrew S. Tomcufcik 《Journal of heterocyclic chemistry》1979,16(7):1345-1347
Reactions of 2,3-dichloroquinoxalines with 2-(hydroxymethyl)piperidine resulted in a series of 1,2,3,4,4a,5-hexahydropyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxaline derivatives. The structures of the products were confirmed by nmr and x-ray crystallography. 相似文献
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A new functional group, the hydroxy group, was inserted into a Betti base by reaction with salicylaldehyde, and the naphthoxazine derivatives thus obtained were converted by ring-closure reactions with formaldehyde, acetaldehyde, propionaldehyde or phosgene to the corresponding naphth[1′2′:5,6][1,3]oxazino[3,2-c][1,3]benzoxazine derivatives. Further, the conformational analysis of these polycyclic compounds by NMR spectroscopy and an accompanying molecular modelling are reported; especially, both quantitative anisotropic ring current effects of the aromatic moieties in these compounds and steric substituent effects were employed to determine the stereochemistry of the naphthoxazinobenzoxazine derivatives. 相似文献
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Bisma Teli Malik Abdul Waseem Showkat Rashid Bilal Ahmad Ganaie Bilal A. Bhat 《Journal of heterocyclic chemistry》2021,58(7):1541-1545
An ultrasonication-assisted synthesis of 2-Aryl-2H-benzo[b][1,4]oxazines and 3-aryl-2H-benzo[b][1,4]thiazin-2-ones has been established by reacting phenacyl bromides with 2-aminophenol and 2-aminothiophenol, respectively. This approach fosters flexibility in generating a diverse range of 1,4-benzoxazines and 1,4-benzothiazinones under catalyst-free reaction conditions. Further scope toward the synthesis of rarely occurring bis-benzoxazine adduct has also been explored, which enabled us to propose the reaction mechanism. 相似文献
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<正>Reactions of the 6-hydroxy-thiopyrano[3,4-c]pyridine-5-carbonitrile derivative 1 withα-halo-carbonyl compounds gave the ortho-substituted intermediates 2a-c which were converted into furo[2,3-b]thiopyrano[4,3-d]pyridines 3a-c by fusion of a furan moiety under basic conditions.Further cyclization of 3a-c led to a fusion of a pyrimidine ring,yielding the tetracyclic products 6,7 and 8.In addition,condensation of 6 with various aromatic aldehydes afforded the corresponding imines 9a,b.Mannich reaction of 7 gave products 10a,b. 相似文献
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The title compounds were synthesized from 3-[bis(2-hydroxyethyl)amino]quinolin-2(1H)-one 11a and 3-[bis(2-hydroxyethyl)amino]pyridin-2(1H)-one 18 respectively. The preparation involved a tandem chlorination/cyclization reaction. 相似文献
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Reaction of 2-chloro-3-(3-chloro-1H-pyrazol-5-yl)quinoxaline and aldehydes does not afford the corresponding N-(α-hydroxyalkylated) derivatives but results in a cyclisation reaction to give a derivative bearing the hitherto undescribed pyrazolo[2′,3′:3,4][1,3]oxazino[5,6-b]quinoxaline system. 相似文献
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An efficient method for the synthesis of novel benzo[b]pyrido[3',2':4,5] thieno[2,3-e][1,6] naphthyridine-8-one derivatives has been developed using a Pictet-Spengler reaction between 4-(3-aminothieno[2,3-b]pyridin-2-yl)quinoline-2-ones, which could be obtained from the alkylation of 4-bromomethylquinoline-2-ones with 3-cyanopyridine-2-thione followed by a Thorpe-Ziegler isomerization, and aromatic aldehydes under p-TsOH as catalysis in good yields. 相似文献
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Cyclization of 2′-benzoyl-4′-chloro-2-[(2-hydroxypropyl)amino]acetanilide (8) and 2′-bcnzoyl-4-ehloro-2-[(3-hydroxypropyl)amino]acetanilide ( 7 ) led to the respective oxazolo (3) and oxazino (5) analogs of 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one. Cyclization of 2′-benzoyl-4′-chloro-2-[2,3-dihydroxypropyl)amino]acetanilide ( 9 ) could produce either the oxazolo ( 4 ) or oxazino ( 10 ) analog. Data is presented to show that cyclization occurred to give the oxazolo (4) analog. 相似文献
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Francesco Savelli Alessandro Boido Iana Vazzana Fabio Sparatore 《Journal of heterocyclic chemistry》1987,24(6):1709-1716
In pursuing the study on compounds obtained by condensation of N-monoalkylated aromatic and hetero-aromatic diamines with α- and β-ketoesters, 7,8,9,10-tetrahydrocyclopenta[e]pyrido[3,2-b][1,4]diazepin-6(5H)-ones 4a, 4b and 5,7,8,10-tetrahydrocyclopenta[e]pyrido[2,3,-b][l,4]diazepin-9H)-ones 5a, 5b were prepared starting from 2,3-diaminopyridine or 2,3-diamino-5-chloropyridine and ethyl 2-oxo-cyclopentanecarboxylate. Compounds 4a,b and 5a,b suffer thermally induced ring contraction to the imidazolone derivatives 8a,b and 7a,b respectively and are unsuitable for preparing diazepinone derivatives. Thus the methylated diazepinones 15, 17 and 18 , stable on heating, were prepared. Compound 17 was transformed into the clozapine analogue 22 , through the diazepinthione 20 and its S-methyl derivative 21 . 相似文献
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Jiaying Yan Yang Zhou Nuonuo Zhang Hui Chen Xiafeng He Shuzhang Xiao Kaibo Zheng 《Research on Chemical Intermediates》2017,43(10):5395-5402
Several novel fused heterocyclic systems which have rings containing N/O or N/S have been synthesized through a facile one-pot method by the treatment of substituted 2-(benzo[d]thiazol-2-yl)phenol and cyanogen bromide in THF and NEt3. This one-pot method contains tough ring-opening of thiazole, special intermolecular rearrangement and ring-closing reactions. The newly synthesized compounds were characterized by HR-MS, 1H-NMR, 13C-NMR spectral data and DFT calculation analysis. 2a was also determined by X-ray crystallographic analysis. 相似文献
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