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1.
Piergiorgio Pecorari Marcella Rinaldi Maria Paola Costi Luciano Antolini 《Journal of heterocyclic chemistry》1991,28(4):891-898
The cyclization reactions, carried out in strongly- or weakly-basic media, are described. Sometimes, 7-amino-2,3-dihydro-3-hydroxymethyl-5H-thiazolo[3,2-a]pyrimidin-5-one is separated out, together with 8-amino-3,4-dihydro-3-hydroxy-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one, as the principal product. A mechanism of reaction, during which the cyclizating agents are changed into oxirane derivatives, is proposed. The results of single-crystal X-ray investigations on 8-amino-3,4-dihydro-3-hydroxy-7-nitroso-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one (R = 0.035 for 1013 reflections), and on 7-hydroxymethyl-6,7-dihydrothiazolo[3,2-a][1,2,3]triazolo[4,5-d]pyrimidin-9(1H)-one (R = 0.027 for 1607 reflections) are reported. 相似文献
2.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2005,41(6):782-786
The products of the reaction of 2-aryl-5-R-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones with aryl bromomethyl ketones are 2-aryl-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones and aryl methyl ketones or 2,5-diaryl[1,3]thiazolo[3,2-b][1,2,4]triazoles and 3-phenyl-2-propenoic acid, depending on the structure of R. The reaction of 2-aryl-5-R-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones with benzyl bromide yields 5-aryl-3-benzylthio-4H-1,2,4-triazoles and 3-aryl-2-propenoyl bromide.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 905–909, June, 2005. 相似文献
3.
Piergiorgio Pecorari Marcella Rinaldi M. Paola Costi Luciano Antolini 《Journal of heterocyclic chemistry》1992,29(6):1449-1455
Derivatives of two new molecular structures, namely, 7,8-dihydro-6H,10H-[1,2,5]thiadiazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]thiazin-10-one and 6,7-dihydro-9H-thiazolo[3,2-a][1,2,5]thiadiazolo[3,4-d][pyrimidin-9-one, and derivatives of N-substituted sulfamic acid, namely, (8-amino-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-on-7-yl)sulfamic acid and (7-amino-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-5-on-6-yl)sulfamic acid, were separated out as by-products in the reduction reaction of 8-amino-3,4-dihydro-7-nitroso-2H,6H-pyrimido[2,1- b][1,3]thiazin-6-one and 7-amino-2,3-dihydro-6-nitroso-5H-thiazolo[3,2-a]pyrimidin-5-one derivatives, respectively, with sodium hydrosulfite. A mechanism of reaction, which hypothesizes the action of sodium hydrosulfite in an asymmetic form, is proposed. The results of single-crystal X-ray investigation on 7,8-dihydro-6H,10H-[1,2,5]thiadiazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]thiazin-10-one (R = 0.032 for 863 reflections) and (8-amino-3,4-dihydro-2H,6H-pyrimido[2,1-b]- [1,3]thiazin-6-on-7-yl)sulfamic acid, sodium salt (R = 0.028 for 3507 reflections) are reported. 相似文献
4.
Braulio Insuasty Henry Insuasty Jairo Quiroga Manuel Nogueras Adolfo Snchez M. Dolores Lpez 《Journal of heterocyclic chemistry》1999,36(4):933-936
New 6-amino and 6,8-diamino-2-aryl-2,3-dihydro-4-styryl-1H-pyrimido[4,5-b][1,4]diazepines were obtained in the reaction of 2,4,5,6-tetraaminopyrimidine 1a and 4,5,6-triaminopyrimidine 1b with one equivalent of the diaryli dene acetones 2 in absolute ethanol with acetic acid as the catalyst. Structure analysis of 6-amino and 6,8-diamino-2-aryl-2,3-dihydro-4-styryl-1H-pyrimido[4,5-b][1,4]diazepines 3a-i, determined by detailed nmr measurements, reveals a high regioselectivity of this reaction. 相似文献
5.
1-Chlorobenzyl isocyanates react with 4-hydroxy-6-methylpyran-2-one and 4-hydroxycoumarin forming 4-aryl-3,4-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]oxazine-2,5-diones. The reaction of 1-aryl-2,2,2-trifluoro-1-chloroethyl isocyanates with the above substrates gives rise to structurally isomeric 2-aryl-2-trifluoromethyl-2,3-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]-oxazine-4,5-diones. 相似文献
6.
A synthesis of 4-N-oxides and of 3-hydroxy derivatives of 1,3-dihydro-2H-benzofuro[3,2-e][1,4]diazepin-2-ones and of 2,3-dihydro-1H-benzofuro[3,2-e][1,4]diazepines is described. Condensation of 2-acetyl- and 2-benzoyl-3-ethoxycarbonylaminobenzofurans with acrylonitrile gave derivatives of 1,2-dihydro- and of 1,2,3,4-tetrahydrobenzofuro[3,2-b]pyridine. 相似文献
7.
The dipolar 1,4-cycloaddition of dichloroketerie to N,N-disubslituled 3-aminomethylene-2,3-dihydro-4-thiochromanones and 3-aminomethylenetelrahydro-4-thiopyranones gave N,N-disubstituted 4-amino-3,3-diehloro-3,4-dihydro-2H,5H-[1]benzolhiopyrano[4,3-b]pyran-2-ones and 4-amino-3,3-dichloro-3,4,7,8-tetrahydro-2H,5H-thiopyrano[4,3-b]pyran-2-ones, respectively, only in the ease of aromatic or strong hindering aliphatic N-substitution. The adducts gave N,N′-disubstituted 4-amino-3-chloro-2H,5H-[1]benzothiopyrano[4,3-b]pyran-2-ones and 4-amino-3-chloro-7,8-dihydro-2H,5H-thiopyrano[4,3-b]pyran-2-ones, respectively, by dehydro-chlorination with DBN. By chromatography on neutral alumina, 3-(2,2-dichloroethylidene)-2,3-dihydro-4-thiochromanone was isolated as an unstable liquid from the reaction between dichloroketerie and 3-diethylaminornethylene-2,3-dihydro-4-thiochromanone. 相似文献
8.
Braulio Insuasty Alfredo Perez John Valencia Jairo Quiroga 《Journal of heterocyclic chemistry》1997,34(5):1555-1558
The reaction of 2,3,6-triaminopyridine 1 and 4,5,6-triaminopyrimidine 2 with one equivalent of the chal-cones 3, in acetic acid, leads to the formation of the 8-amino-2,3-dihydro-1H-pyrido[2,3-b][1,4]diazepine and 6-amino-2,3-dihydro-1H-pyrimido[4,5-b][1,4]diazepine derivatives 4 and 5 . The products were characterized by NMR techniques such as 13C, 1H, and DEPT including selective 13C{1H} decoupling experiments. 相似文献
9.
A rapid, efficient and benign protocol has been developed for the construction of potentially biologically active furo[2′,3′:4,5]pyrimido[2,1-b][1,3]benzothiazole derivatives as major products along with (3E)-3-[(alkylamino)methylene]-2H-pyrimido[2,1-b][1,3]benzothiazole-2,4(3H)-dione derivatives as minor products using a one-pot, multi-component reaction of isocyanides, aromatic aldehydes and 2-hydroxy-4H-pyrimido[2,1-b][1,3]benzothiazol-4-one. The significant features of this protocol are the readily available and low-cost starting materials, short reaction time, mild reaction conditions, high yield of products and avoidance of toxic solvents and catalysts. Structures of compounds 4b and 5a were confirmed from single crystal X-ray studies. 相似文献
10.
Issa Yavari Zinatossadat Hossaini Maryam Sabbaghan Majid Ghazanfarpour-Darjani 《Monatshefte für Chemie / Chemical Monthly》2007,138(7):677-681
Summary. The 1,3-dipolar intermediates generated by addition of isoquinoline, to dialkyl acetylenedicaboxylates are trapped by N-alkylisatins to produce dialkyl 1,2-dihydro-2-oxo-1-alkylspiro[3H-indol-3,2′-[2H,11bH][1,3]oxazino[2,3-a]isoquinoline]-3′,4′-dicarboxylates in excellent yields. The reaction of isoquinoline, quinoline, or pyridine with dimethyl
acetylenedicarboxylate in the presence of ninhydrin led to dimethyl 1,2-dihydro-1,3-dioxospiro[3H-indene-3,2′-[2H,11bH][1,3]oxazino[2,3-a]isoquinoline]-3′,4′-dicarboxylate, dimethyl 1,2-dihydro-1,3-dioxospiro[3H-indene-3,3′[3H,4aH][1,3]oxazino[3,2-a]quinoline]-1,2-dicarboxylate, or dimethyl 1,2-dihydro-1,3-dioxospiro[3H-indene-3,2′-[2H,9aH]pyrido[2,1-b][1,3]oxazino]-3,4-dicarboxylate. 相似文献
11.
The reactions of dimethyl acetylenecarboxylate with 3,4,5,6-tetrahydro-2H-1,2,4-triazepine-3-thiones and 4,5-dihydro-1H-pyrazole-1-carbothioamides are convenient methods for the synthesis of 7,8-dihydrothiazolo[3,2-b][1,2,4]triazepin-3-ones derivatives and methyl esters of (2Z)-[2-(4,5-dihydro-1H-pyrazol-1-yl)-4-oxo-1,3-thiazol-5(4H)-ylidene]acetic acids, respectively. The reaction of methyl propynoates with 4,5-dihydro-1H-pyrazole-1-carbothioamides or with 5,5,7-trimethyl-2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thione gives 2-(4,5-dihydro-1H-pyrazol-1-yl)-4H-1,3-thiazin-4-ones. 相似文献
12.
Pyrolytic conversion of [1,2,4]triazino[3,4-b][1,3,4]thiadiazin-4-ones, [1,3,4]thiadiazino[2,3-b]quinazolin-10-ones and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines into their corresponding pyrazolo[5,1-c][1,2,4]triazin-4-ones, pyrazolo[4,3-b]quinazolin-9-ones and pyrazolo[5,1-b][1,2,4]triazoles via desulfurization ring contraction is described. The starting condensed 1,3,4-thiadiazines were prepared from the corresponding readily available 4-amino-3-thioxo-1,2,4-triazin-5(4H)-ones, 3-amino-2,3-dihydro-2-thioxoquinazolin-4(1H)-one and 4-amino-3(2H)-thioxo-1,2,4-triazoles upon reaction with the appropriate α-haloketones in two steps, or directly in one step in ethylpyridinium tetrafluoroborate (ionic liquid, IL). 相似文献
13.
Britsun V. N. Esipenko A. N. Kudryavtsev A. A. Lozinskii M. O. 《Russian Journal of Organic Chemistry》2004,40(2):232-238
A new procedure for preparation of 2-R-5-aryl-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones by condensation of 5-R-1,2,4-triazole-3-thiones with 3-arylacryloyl chlorides was developed. The thiazine ring of the [1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones is easily cleaved by treating with ammonia and hydrazine affording amides and hydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-ylsulfanyl)propanoic acids. The latter react with isothiocyanates furnishing carbamoyl thiohydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-ylsulfanyl)propanoic acids that in alkaline media undergo cyclization into 4-aryl-5-[2-(4H-1,2,4-triazol-5-ylsulfanyl)-2-phenylethyl]-2,4-dihydro-3H-1,2,4-triazole-5-thiones. 相似文献
14.
V. N. Britsun A. N. Esipenko A. N. Chernega M. O. Lozinskii 《Russian Journal of Organic Chemistry》2005,41(1):108-113
3-Aryl-1,2,4-triazole-5-thiones react with dimethyl acetylenedicarboxylate and methyl 3-phenyl-propynoate to afford the corresponding 5-substituted 2-aryl-7H-[1,2,4]triazolo[3,2-b][1,3]thiazin-7-ones. Treatment of 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones with alkalies leads to formation of 3-(benzimidazol-2-ylsulfanyl)-3-arylpropionic acids, their reaction with methyl p-toluenesulfonate yields 1-(3-methyl-2-thioxo-2,3-dihydro-1N-benzimidazol-1-yl)-3-phenyl-2-propen-1-one, and oxidation with hydrogen peroxide gives benzimidazole-2-sulfonic acid and 3-aryl-2-propenoic acids.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 109–114.Original Russian Text Copyright © 2005 by Britsun, Esipenko, Chernega, Lozinskii. 相似文献
15.
N. F. Kirillov A. G. Gavrilov M. I. Vakhrin 《Russian Journal of Organic Chemistry》2012,48(3):368-372
Methyl 1-bromocyclopentanecarboxylate and methyl 1-bromocyclohexanecarboxylate reacted with zinc and 2-arylmethylidene-2,3-dihydro-1H-inden-1-ones or 2-arylmethylidene-3,4-dihydronaphthalen-1(2H)-ones to give 4′-aryl-4′,5′-dihydro-2′H-spiro[cyclopentane(cyclohexane)-1,3′-indeno[1,2-b]pyran]-2′-ones or 4-aryl-5,6-dihydrospiro[benzo[h]chromene-3,1′-cyclopentane(cyclohexane)]-2(4H)-ones, respectively. 相似文献
16.
Norton P. Peet Shyam Sunder Robert J. Barbuch Michael R. Whalon John C. Huffman 《Journal of heterocyclic chemistry》1988,25(2):543-547
The reaction of 2-hydrazinobenzothiazole (1) with ethyl acetoacetate has twice been reported to yield a fused triazepinobenzothiazolone, namely, 3-methyl[1,2,4]triazepino[3,4-b]benzothiazol-5(4H)-one (4). We have repeated this work and reassigned the reaction product as 2-(2-benzothiazolyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one (5) on the basis of X-ray crystallography. 相似文献
17.
N. N. Smolyar N. N. Troyan A. B. Vasilechko D. A. Lomov Yu. M. Yutilov 《Russian Journal of Organic Chemistry》2007,43(11):1706-1709
Nitration of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one gave its 5-nitro derivative which was subjected to alkylation with dimethyl sulfate, diethyl sulfate, and benzyl(dimethyl)phenylammonium chloride. The resulting 1,3-dimethyl-, 1,3-diethyl-, and 1,3-dibenzyl-5-nitro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones were reduced to the corresponding 1,3-dialkyl-5-amino-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, and the latter reacted with itaconic acid to produce 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids. 1-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acid was obtained by analogous reaction with 5-amino-2,3-dihydro-1H-imidazo[4,5-b]-pyridin-2-one. 相似文献
18.
Yu. M. Yutilov Kh. Ya. Lopatinskaya N. N. Smolyar S. V. Gres’ko 《Russian Journal of Organic Chemistry》2005,41(4):575-579
Chlorination and bromination of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one and its N-methyl-substituted derivatives in acetic acid at 90–95°C leads to formation of the corresponding 5,6-dichloro(dibromo)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones. Iodination of the same substrates with ICl under analogous conditions yields 6-iodo derivatives. Chlorination of 6-iodo-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one is accompanied by replacement of the iodine atom by chlorine with formation of 5,6-dichloro-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one. Bromination of 6-bromo- and 6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones gives 5,6-dibromo- and 5-bromo-6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, respectively.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 586–589.Original Russian Text Copyright © 2005 by Yutilov, Lopatinskaya, Smolyar, Gres’ko. 相似文献
19.
R. Friary 《Journal of heterocyclic chemistry》1978,15(1):77-80
Reductive cyclization of 2-methylthio-1-(2-nitrobenzyl)-6-pyrimidones with stannous chloride and acetic acid in methanol gives 6,11-dihydro-6H-pyrimido[2,1-b]quinazolin-4-ones, and, with trialkylphosphites, 6,11-dihydro-11-alkylpyrimido[2,1-b]quinazolin-4-ones. 相似文献
20.
Piergiorgio Pecorari Marcella Rinaldi Maria Paola Costi 《Journal of heterocyclic chemistry》1989,26(6):1701-1705
Derivatives of two new molecular structures, namely, [1,3]thiazino[3,2-a]purine and [1,2,3]triazolo[4,5-d]-[1,3]thiazino[3,2-a]pyrimidine, were synthesized together with other heterocyclic compounds. Retrosynthetic analysis of their molecular skeletons suggested a simple way of obtaining 3,4-dihydro-7,8-diamino-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one, which is a useful intermediate for their synthesis. This intermediate and the thiazole homologue were obtained directly by reaction of 5,6-diamino-2,3-dihydro-2-thioxo-4(lH)-pyrimidi-none with 1,3- or 1,2-dibromoalkane, respectively. 相似文献