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1.
The intramolecular electrophilic substitution in 6-functionalized 1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-diones was used for the synthesis of pyrimido[4′,5′:3,4]-pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione, pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,2,4]benzo-triazine-8,10(7H,9H)-dione, and 2H-pyrimido[4′,5′:3,4]pyrrolo[1,2-a]indole-2,4,11(1H, 3H)-trione derivatives.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2180–2185, December, 2006. 相似文献
2.
G. V. Mokrov A. M. Likhosherstov V. P. Lezina T. A. Gudasheva I. S. Bushmarinov M. Yu. Antipin 《Russian Chemical Bulletin》2011,60(8):1694-1702
Reactions of methyl 2-(2-formyl-1H-pyrrol-1-yl)alkanoates with unsubstituted aliphatic 1,2-, 1,3-, and 1,4-diamines gave N-unsubstituted pyrrolo[2,1-c]-1,3-diazacycloalkano[1,2-a]-pyrazinones. Some of them show ring-chain tautomerism. Transformations of these compounds led to a number of novel heterocyclic systems: 2,10-dihydro-3H,5H-imidazo[1,2-a]-pyrrolo[1,2-d]pyrazines, 2,3,4,11-tetrahydro-6H-pyrrolo[1??,2??:4,5]pyrazino[1,2-a]pyrimidines, 1,2,3,5,6,10b-hexahydroimidazo[1,2-a]pyrrolo[2,1-c]pyrazines, 1,3,4,6,7,11b-hexahydro-2H-pyrrolo[2??,1??:3,4]pyrazino[1,2-a]pyrimidines, and 2,3,4,5,6,7-hexahydro-1H-pyrrolo[2,1-c]-[1,4,7]triazacycloundecin-8(9H)-one. 相似文献
3.
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
4.
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
5.
V. L. Gein V. V. Mishunin E. P. Tsyplyakova M. I. Vakhrin P. A. Slepukhin 《Russian Journal of Organic Chemistry》2011,47(7):1077-1082
Fusion of methyl 4-(2-thienyl)-2,4-dioxobutanoate with 1H-tetrazol-5-amine monohydrate and aromatic aldehyde gave methyl 7-aryl-6-(2-thenoyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylates which reacted with an equimolar amount of hydrazine hydrate at 180–190°C under solvent-free conditions
to produce 9-aryl-8-(2-thienyl)-4,9-dihydrotetrazolo[1′,5′: 1,2]pyrimido[4,5-d]pyridazin-5(6H)-ones. 相似文献
6.
4,8-Dimethyl-6,7,8,9-tetrahydropyrido[4′,3′:4,5]thieno[2,3-e][1,2,4]triazolo[3,4-a]-4H-pyrimidin-5-ones, 7-methyl-2,3,6,7,8,9-hexahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrrolo[1,2-a]-1H, 10H-pyrimidin-10-one, 8-methyl-1,2,3,4,7,8,9,10-octahydropyrido[4′,3′:4,5]thieno[2,3-d]-11H-pyrimidin-11-one, and 9-methyl-2,3,4,5,8,9,10,11-octahydro[4′,3′:4,5]thieno[2,3-d]azepino-[1,2-a]-1H, 12H-pyrimidin-12-one which consist four new heterocyclic ring systems were synthesized from 2-amino-3-carbethoxy-5-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine. 相似文献
7.
V. A. Glushkov G. F. Krainova O. A. Maiorova V. I. Karmanov A. A. Gorbunov P. A. Slepukhin 《Russian Journal of Organic Chemistry》2012,48(4):575-581
Addition of 1,3,3-trimethyl-3,4-dihydroisoquinolines to N-benzylideneanilines gives substituted N-[2-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-1-phenylethyl]anilines, whereas 2′,5′,5′-trimethyl-4′,5′-dihydro-4H-spiro[naphthalene-1,3′-pyrrol]-4-one reacts with N-benzylideneanilines along two pathways involving cyclization to substituted 2,3,3a,4,10,11-hexahydrobenzo[f]pyrrolo[2,3-d]quinolin-5(1H)-ones or elimination of the aniline residue with formation of substituted 5′,5′-trimethyl-2-styryl-4′,5′-dihydro-4H-spiro[naphthalene-1,3′-pyrrol]-4-ones. 相似文献
8.
A. Yu. Potapov A. S. Shestakov V. N. Verezhnikov Kh. S. Shikhaliev 《Russian Journal of Organic Chemistry》2011,47(7):1074-1076
Three-component cyclization of 4-aryl-1,4-dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazin-2-amines with formaldehyde and primary amines gave the corresponding 6-unsubstituted or 6-aryl-2-alkyl-2,3,4,6-tetrahydro-1H-[1,3,5]triazino[1′,2′:3,4][1,3,5]triazino[1,2-a]benzimidazoles. 相似文献
9.
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
10.
M. A. Kukaniev S. Sh. Shukurov U. Norov Yu. Khodzhiboev 《Russian Chemical Bulletin》1999,48(2):364-366
2-R-5-Imino-6H-1,3,4-thiadiazolo[3,2-a]pyrimidin-7-ones react with aromatic and heterocyclic aldehydes in the presence of Et3N to give condensation products on the methylene group, which react with carbon disulfide to yield the corresponding 2,6-disubstituted
8-thioxo-9,9a-dihydro-1,3,4-thiadiazolo[3′,2′∶1,2]pyrimidino[5,6-d]1,3-thiazin-5-ones.
Deceased.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 366–368, February, 1999. 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.
Mosselhi A. N. Mosselhi 《Monatshefte für Chemie / Chemical Monthly》2002,133(10):1297-1304
Summary. Reaction of 6-Amino-2-thiouracil with hydrazonoyl halides yielded regioselectively 7-amino-1,3-disubstituted-1,2,4-triazolo[4,3-a]pyrimidine derivatives. Upon treatment with methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate, the corresponding methyl (Z)-2-benzoylamino-3-([1,2, 4]triazolo[4,3-a]pyrimidin-7-yl)-amino propenoates were obtained which cyclized in the presence of sodium ethoxide to afford novel derivatives
of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6-(1H,8H)-diones.
E-mail: mosselhi@chem-sci.cairo.eun.eg
Received February 8, 2002; accepted (revised) March 18, 2002 相似文献
13.
Neringa Kleizien? Virgin? Amankavi?ien? Ulf Berg Carsten Schicktanz Klaus Schlothauer Algirdas ?a?kus 《Monatshefte für Chemie / Chemical Monthly》2006,43(9):1109-1117
Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with 5-nitrosalicylaldehyde afforded 1′-[(N-monosubstituted carbamoyl)methyl]indoline nitrospirobenzopyrans.
Treatment of the latter with strong base led to the formation of a mixture of cis/trans-5a,13-methano-1,3-benzoxazepino[3,2-a]indoles. Results of semiempirical calculations gave evidence that such a transformation of nitrospirobenzopyrans to bicyclic
indole derivatives could proceed via a single transition state, where the negatively charged carbon atom attacks the vinylic double bond of the spiropyran system. 相似文献
14.
A. L. Kurlovich V. A. Tarasevich N. G. Kozlov 《Russian Journal of Organic Chemistry》2009,45(10):1503-1508
Condensation of 2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-carbaldehyde with naphthalen-1-amine and cyclohexane-1,3-dione, methyl
2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate, or dimedone gave the corresponding 7-(2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-yl)-7,8,9,10,11,12-hexahydro-12H-benzo[c]acridin-8-ones. The reaction of 2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-carbaldehyde with naphthalen-1-amine and indan-1,3-dione
produced 7-(2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-yl)-8H-benzo[h]indeno[1,2-b]quinolin-8-one. 7-(2′-Hydroxy-1,1′: 3′,1″-terphenyl-5′-yl)-7,8,9,10,11,12-hexahydrobenzo[b][1,10]phenanthrolin-8-ones were obtained by three-component condensation of 2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-carbaldehyde
with quinolin-8-amine and cyclohexane-1,3-dione, methyl 2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate, or dimedone. 相似文献
15.
V. S. Tolkunov A. B. Eres’ko A. I. Khizhan A. V. Mazepa G. V. Palamarchuk O. V. Shishkin S. V. Tolkunov 《Chemistry of Heterocyclic Compounds》2012,48(4):666-671
A series of previously unknown 2-([1]benzothieno[2,3-c]pyridin-1-yl)benzoic acids and 8,13b-dihydro-[1]benzothieno[2',3':3,4]pyrido[2,1-a]isoindol-5(7 H)-ones has been synthesized using domino reactions, taking place at the cyclization of 2-[3-oxo-4-(phenylsulfanyl)butyl]-1,3-isoindolinediones in polyphosphoric acid. 相似文献
16.
O. Yu. Smirnov A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》2008,57(10):2180-2184
Thermolysis of 7-azido-6-(2H-1,2,3-triazol-2-yl)-1,2,3,4-benzotetrazine 1,3-dioxide and 7-azido-6-(1H-1,2,3-triazol-1-yl)-1,2,3,4-benzotetrazine 1,3-dioxide gives rise to the new heterocyclic systems: 6,10-dehydro-6H,10H-[1,2,3]triazolo[1′,2′:2,3][1,2,3]triazolo[4,5-g]-[1,2,3,4]benzotetrazine 2,4-dioxide and 6,8-dehydro-6H,8H-[1,2,3]triazolo[1′,2′:1,2][1,2,3]-triazolo[4,5-g][1,2,3,4]benzotetrazine 2,4-dioxide, respectively, their thermal stability and spectral properties have been studied. 相似文献
17.
1,4-Naphthoquinone ( 1 ) was transformed with alkyl 2-aminofumarates 2 into 2H-naphtho[1,2-b]pyran-2-ones 3 and 4 , which served as intermediates in the synthesis of 7, 8 and 13 , which are derivatives of two new heterocyclic systems: naphtho[2′,1′:5,6]pyrano[3,4-d][1,3]oxazine and naphtho[1′,2′:5,6]pyrano[3,4-d]pyrimidine. 相似文献
18.
Mosselhi A. N. Mosselhi 《Monatshefte für Chemie / Chemical Monthly》2002,29(1):1297-1304
Reaction of 6-Amino-2-thiouracil with hydrazonoyl halides yielded regioselectively 7-amino-1,3-disubstituted-1,2,4-triazolo[4,3-a]pyrimidine derivatives. Upon treatment with methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate, the corresponding methyl (Z)-2-benzoylamino-3-([1,2, 4]triazolo[4,3-a]pyrimidin-7-yl)-amino propenoates were obtained which cyclized in the presence of sodium ethoxide to afford novel derivatives
of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6-(1H,8H)-diones. 相似文献
19.
Neringa Kleizienė Virginė Amankavičienė Ulf Berg Carsten Schicktanz Klaus Schlothauer Algirdas Šačkus 《Monatshefte für Chemie / Chemical Monthly》2006,137(8):1109-1117
Summary. Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with 5-nitrosalicylaldehyde afforded 1′-[(N-monosubstituted carbamoyl)methyl]indoline nitrospirobenzopyrans.
Treatment of the latter with strong base led to the formation of a mixture of cis/trans-5a,13-methano-1,3-benzoxazepino[3,2-a]indoles. Results of semiempirical calculations gave evidence that such a transformation of nitrospirobenzopyrans to bicyclic
indole derivatives could proceed via a single transition state, where the negatively charged carbon atom attacks the vinylic double bond of the spiropyran system. 相似文献
20.
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