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1.
Martin Winterwerber Rouzita Geiger Ursula Predoiu Hans-Hartwig Otto 《Monatshefte für Chemie / Chemical Monthly》2006,137(11):1441-1451
Summary. Reactions of cyanomethanesulfonamides with aromatic aldehydes in the presence of AcOH and piperidine produced the addition products, the 1-cyano-2-arylethenesulfonamides, whereas reactions with benzonitrile
yielded the 2-amino-1-cyano-2-phenylethenesulfonamides only when done in THF with BuLi. No addition products were isolated from the analogue reactions with 2-hydroxybenzaldehyde (salicylaldehyde). Instead,
we obtained 2-imino-2H-chromene-3-sulfonamides with good to excellent yields. These 2H-chromene derivatives allowed a number of transformations, from which the reactions with orthoformates opened an approach
to the hitherto unknown benzopyrano[3,2-e] [1,2,4]thiadiazine ring system. 相似文献
2.
The reaction of 5a-acetyl-6-ethoxycarbonyl-5a,6a-dihydro-6H-cyclopropa[e]pyrazolo[1,5-a]pyrimidine-3-carbonitrile ( 1a ) with benzylamine gave ethyl l-benzyl-5-cyano-8a,9-dihydro-2-methyl-1H-pyrrolo[3,4-e]-pyrazolo[1,5-a]pyrimidine-8a-carboxylate ( 2a ), in addition to 5-acetyl-3-benzylamino-1-(4-cyanopyrazol-3-yl)- 2-pyridone ( 3 ). Reaction of 1a with aniline gave ethyl 6-acetyl-8-anilino-3-cyano-7,8-dihydro-4H-pyrazolo-[1,5-a][1,3]diazepine-8-carboxylate ( 4 ), in addition to ethyl 3-cyano-7-methyl-6-pyrazolo[1,5-a]pyrimidine-acrylate ( 5 ). On the other hand, the same reactions of 1b with benzylamine or aniline gave 2b or 8b , respectively. Though catalytic hydrogenation of 1a over 5% palladium-carbon proceeded by ring fission of cyclopropane ring to give 9 , 1a (or 1b ) afforded 4,5-dihydro derivatives ( 13 or 15 ) by catalytic hydrogenation over platinum oxide. The reactivity of 5-methoxy-4,5,5a,6a-tetrahydro-6H-cyclopropa[e]pyrazolo[1,5-a]pyrimidine ( 16 ), which are related analogs of 1a,b , is also described. 相似文献
3.
The reactions of 3-acetyl-4-ethoxycarbonyl- or 3,4-diethoxycarbonylpyrrolo[1,2-a]pyrimidine derivatives 7a,b , which were prepared by condensation of the 2-aminopyrrole ( 4 ) with ethyl 3-ethoxymethylene-2,4-dioxovalerate ( 5a ) or ethyl ethoxymethyleneoxaloacetate ( 5b ), with diazomethane are described. Thus, reaction of 7a , with diazomethane gave ethyl 2a-acetyl-7-cyano-2a,3a-dihydro-5,6-dimethyl-3H -cyclopropa[e]pyrrolo[1,2-a]pyrimidine-3a-carboxylate ( 11 ) in 74% yield, which was readily transformed into the 1-pyrrol-2-yl-pyrrole ( 18 ) by treatment with potassium hydroxide. On the other hand, reaction of 7b with diazomethane afforded three products whose structures were assigned as diethyl 7-cyano-2a,3a-dihydro-5,6-dimethyl-3H-cyclopropa[e]pyrrolo[1,2-a]pyrimidine-2a,3a-carboxylate ( 20 ), 6-cyano-7,8-dimethyl-3a,3b,5,9a-tetrahydro-4H -aziridino[c]-1H or 3H-pyrazolo[3,4-e]pyrrolo[1,2-a]pyrimidine-3a,9a-dicarboxylates ( 21,22 ). Ring Transformation of 20 to 25 was not observed. 相似文献
4.
Andre Rosowsky Adrienne S. Dey Josephine Battaglia Edward J. Modest 《Journal of heterocyclic chemistry》1969,6(5):613-622
As part of a search for new antifolic, antimalarial, and antitumor agents, a series of 2,4-diamino-9H-indeno[2,1-d]pyrimidines was prepared by condensation of guanidine with substituted 2-alkoxy-3-cyano-1H-indenes. Base-catalyzed cyclization of 1,2-bis(cyanomethyl)benzenes afforded 2-amino-3-cyano-1H-indenes, which were converted into 3-cyano-2-methoxy-1H-indenes by acid hydrolysis and treatment of the resultant 1-cyano-2-indanones with diazomethane. Alternatively, 2-amino-3-cyano-1H-indenes could be transformed directly into 2-ethoxy-3-eyano-1H-indenes by reaction with ethanol and sulfuric acid. The 2,4-diamino-9H-indeno[2,1-d]-pyrimidines represent a new type of planar, tricyclic pyrimethamine analog, in which free rotation of the phenyl and pyrimidine rings is prevented by means of a methylene bridge. 相似文献
5.
Yoshihisa Kurasawa Megumi Kanoh Yumiko Kamigaki Mari Okiyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1988,25(3):1015-1018
The reactions of the pyrazole-5-diazonium salt 3 with malononitrile and ethyl cyanoacetate gave 4-amino-3-cyano-8-ethoxycarbonylpyrazolo[5,1-c][1,2,4]triazine 7 and 4-amino-3,8-bisethoxycarbonylpyrazolo[5,1-c]-[1,2,4]triazine 8 , whose reactions with p-chloroaniline hydrochloride afforded 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)amidinopyrazolo[5,1-c][1,2,4]triazine 9 and 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)car-bamoylpyrazolo[5,1-c][1,2,4]triazine 10 , respectively. The reactions of 7 and 8 with o-phenylenediamine di-hydrochloride provided 9-ethoxycarbonyl-13H-spiro[benzimidazole-2′(3′H),6(5H)-pyrazolo[1,5′:3,4][1,2,4]tri-azino[5,6-b][1,5]benzodiazepine] hydrochloride 11a and 9-ethoxycarbonyl-6-oxo-13H-5,6-dihydropyrazolo-[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzodiazepine 12 , respectively. The antifungal activity of the above compounds was described. 相似文献
6.
John P. Paolini Frank P. Palopoli Louis J. Lendvay John Huffman 《Journal of heterocyclic chemistry》1987,24(3):549-553
The reaction of 2-aminopyridine, o-phthaldehydic acid and potassium cyanide gave pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one, which upon treatment with propargylbromide, yielded both O and N alkylated products. 2-Aminopyridine, o-phthaldehyde and potassium cyanide gave 1-cyano-2-(2-pyridyl)isoindole which rearranged in acid to give the previously unreported parent pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinole. Structures were confirmed using uv, ir, nmr and x-ray spectroscopy. 相似文献
7.
The reactions of 6-methoxybenzo[b]furan-3(2H)-one with 2-aryl-1,1-dicyanoethylenes and malononitrile or with aromatic aldehyde and two moles of malononitrile afford 2-amino-4-aryl-1,3-dicyano-7-methoxydibenzo[b,d]furans. The reactions of benzo[b]thiophen-3(2H)-one with 2-aryl-1,1-dicyanoethylenes or with aromatic aldehyde and one mole of malononitrile produce 2-amino-4-aryl-3-cyano-4H-benzothieno[3,2-b]pyrans. 相似文献
8.
Diversity in Gold‐Catalyzed Formal Cycloadditions of Ynamides with Azidoalkenes or 2H‐Azirines: [3+2] versus [4+3] Cycloadditions
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Samir Kundlik Pawar Rajkumar Lalji Sahani Prof. Dr. Rai‐Shung Liu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(30):10843-10850
Gold‐catalyzed cycloadditions of ynamides with azidoalkenes or 2H‐azirines give [3+2] or [4+3] formal cycloadducts of three classes. Cycloadditions of ynamides with 2H‐azirine species afford pyrrole products with two regioselectivities when the Cβ‐substituted 2H‐azirine is replaced from an alkyl (or hydrogen) with an ester group. For ynamides substituted with an electron‐rich phenyl group, their reactions with azidoalkenes proceed through novel [4+3] cycloadditions to deliver 1H‐benzo[d]azepine products instead. 相似文献
9.
Ivanov A. S. Tugusheva N. Z. Alekseeva L. M. Granik V. G. 《Russian Chemical Bulletin》2003,52(5):1182-1189
Two routes to consecutive functionalization of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (1a) at positions 3 and 10 were developed. Oxidation of compound 1a with m-chloroperbenzoic acid in acetone leads to 3-chloro-4-cyano-10-oxobenzo[b][1,6]naphthyridine, while in acetic acid, the reaction gives 3-chloro-4-cyano-10-(3-chlorobenzoyloxy)-5-hydroxy-5,10-dihydrobenzo[b][1,6]naphthyridine. The reactions of 1a with some C-nucleophiles give -adducts at position 10. The reactions of N,N-dimethylamide acetals with chloride 1a leads to 4-cyano-3-dimethylaminobenzo[b][1,6]naphthyridine. 相似文献
10.
The 3-cyano-4,6-dimethyl-2(1H)-pyridinethione was condensed with benzaldehyde in basic solution leads to styryl-3-cyano-2(1H)-pyridinethiones. Treatment of cinnamicaldehyde with cyanothioacetamide to give cinnamylidencyanothioacetamide, which can be cyclized with the appropriate ketones to afford the 3-cyano-5,6-polymethylene-4-styryl-2(1H)-pyridinethione derivatives. The polyfunctionally substituted 3-aminothieno[2,3-b]pyridine derivatives were obtained in good yield by cyclization of 3-cyano-2(1H)-pyridinethione derivatives with appropriate α-halogeno carbonyl compounds and nitrile, respectively. 相似文献
11.
Shunsaku Shiotani Youichi Tsukamoto Yukiko Kawahara Hideo Saitoh Toshimasa Ishida Yasuko In 《Journal of heterocyclic chemistry》1996,33(6):1967-1976
The photocycloaddition of furo[2,3-c]pyridin-7(6H)-one ( 1 ) and its N-mefhyl derivative ( 1-Me ) to acrylonitrile has been studied. The structures of the photoadducts isolated by colum chromatography were determined by the nuclear magnetic resonance spectroscopy and single crystal X-ray analysis. The cyclo-addition of 1 afforded an adduct 2 at the carbonyl oxygen and 8-cyano-8,9-dihydrofuro[d]azocin-7(6H)-one ( 3 ), and the addition of 1-Me the N-methyl derivative 3-Me of 3 , (9S*)-9-cyano-6-methyl-3a,7a-dihydro-3a,7a-ethanofuro[2,3-c]pyridin-7(6H)-one ( 4 ), (2S*, 2aR*, 7bR*)- ( 5 ) and (1R*, 2aS*, 7bS*)-2-cyano-3-methyl-4-oxo-1,2,2a,3,4,7b-hexahydrocyclobuta[e]furo[2,3-c]pyridine ( 6 ). 相似文献
12.
Štefan Marchalín Dušan Ilavský Milan Bruncko 《Monatshefte für Chemie / Chemical Monthly》1989,120(12):1101-1105
Summary Good yields of substituted 5-(5R-2-furyl)-4H-pyrano[2,3-d]pyrimidines4 were obtained in the reaction of 2-ethoxymethyleneamino-3-cyano-4H-pyranes2 with ammonia. Compounds2 were prepared by the condensation of the starting 2-amino-5-acetyl-3-cyano-6-methyl-4H-pyranes1 with ethyl orthoformate. Spectral properties of the bicyclic system4 in relation to compounds3 are discussed. 相似文献
13.
The substitution and addition reactions of the 2H[1]benzothiéno[2,3-d]phyridazinethione-1 and the 3H[1]benzothiéno[2,3-d]pyridazinethione-4 gave N- or S-substituted derivatives whose structures were identified by 1R and NMR spectroscopy. 相似文献
14.
The reaction of 4-chloro-5-cyano-2-methylthiopyrimidine (I) with ethyl mercaptosuccinate (II) in refluxing ethanol containing sodium carbonate has afforded diethyl 3-amino-2-(methyl-thio)-7H-thiopyrano[2,3-d]pyrimidine-6,7-dicarboxylate (IV). Displacement of the methylthio group in IV with hydrazine gave the corresponding hydrazino derivative which underwent Schiff base formation with benzaldehyde or 2,6-dichlorobenzaldehyde. Treatment of IV in refluxing acetic anhydride afforded the corresponding diacetylated amino derivative. Partial saponification of IV with sodium hydroxide gave 5-amino-2-(methylthio)-7H-thiopyrano-[2,3-d]pyrimidine 6,7-dicarboxylic acid 6 ethyl ester (VIII). The reaction of 4-amino-6-chloro-5-cyano-2-phenylpyrirnidine (XI) with II resulted in the formation of ethyl 4-amino-6-(ethoxy-carbonyl)-5,6-dihydro-5-amino-2-phenylthieno[2,3-d]pyrimidine-6-acetate (XIII) which when subjected to hydrolysis gave ethyl 4,5-diamino-2-phenylthieno[2,3-d]pyrimidine-6-acetate isolated as the hydrochloride (XIV). Diazotization of IV with sodium nitrite in acetic acid unexpectedly afforded diethyl 5-(acetyloxy)-6,7-dihydro-6-hydroxy-2-(methylthio)-5H-thio-pyrano[2,3-d]pyrimidine-6,7-diearboxylate (XV). Several structural ambiguities were resolved by ir and pmr spectra. 相似文献
15.
4,6-Dimethyl-2H-thieno[2,3-b]pyridin-3-one reacts with 2-aryl-1,1-dicyanoethylenes or an aromatic aldehyde/ketone (cyclohexanone and piperidone derivatives) and malononitrile to give substituted 2-amino-3-cyano-7,9-dimethyl-4H-pyrano[2",3":4,5]thieno[2,3-b]pyridines. 相似文献
16.
Carlos Peinador Vicente Ojea Jos Ma. Quintela 《Journal of heterocyclic chemistry》1992,29(7):1693-1702
Ready, convenient synthesis for 8-cyano-7-ethoxy-4-oxo-9-phenyl-2-substituted-1,2,3,-4-tetrahydropyrido-[3′,2′:,4,5]thieno[3,2-d]pyrimidines 5 , 8-cyano-7-ethoxy-4-oxo-9-phenyl-2-substituted-3,4-dihydropyrido[3′,2-: 4,5]thieno[3,2-d]pyrimidines 6 , 4-chloro-8-cyano-7-ethoxy-9-phenyl-2-substitutedpyrido[3′,2′:4,5]thieno[3,2-4 -pyrimidines 7 and 8-cyano-7-ethoxy-2-(2′-nitrophenyl)-9-phenyl-4-substitutedpyrido[3′,2′:4,5]thieno[3,2- d ]pyrimidines 8-18 from 2-chloro-3,5-dicyano-6-ethoxy-4-phenylpyridine 1 via 3,5-dicyano-6-ethoxy-2-mercapto-4-phenylpyridine 2 and aminocarboxamide 4 are reported. In addition, the reaction of hydrazino derivative 12 with reagents such as formic acid and triethyl orthoformate yielded the fused tetraheterocyclic 8-cyano-9- ethoxy-5-(2′-nitrophenyl)- 7-phenylpyrido[3′,2′:4,5]thieno[2,3-e]-1, 2,4-triazolo[4,3-c]pyrimidine system 19 . 相似文献
17.
Charles A. Lovelette 《Journal of heterocyclic chemistry》1979,16(3):555-560
A convenient synthesis of 3-amino-6-hydrazino-5(2H)[1,2,4]triazinone 4 has been developed and a study of the reactions of 4 with aliphatic acids, orthoesters and miscellaneous active carbonyl reagents has been undertaken. When 4 was refluxed in either neat acid or orthoester in dimethylformamide, a facile ring closure reaction with the N-1 nitrogen of the 1,2,4-triazine ring occurs affording a novel series of 3-aIkyl(aryl)-8(5H)-s-triazolo[3,4-f] [1,2,4]triazinones ( 6–11 ). Ring closure with carbon disulfide and cyanogen bromide is also reported affording 6-amino-3(2H)thio-8(5H)-s-triazolo[3,4-f] [1,2,4]triazinone 12 and 3,6-diamino-8(5H)-s-triazolo-[3,4-f] [1,2,4]triazinone 14 , respectively. In addition 4 has been converted into 3-amino-6-azido-5(2H)-1,2,4-triazinone 15 which was employed in a study of azide-tetrazole equilibrium affording 6-amino-8(5H)tetrazolo[1,5-f][1,2,4]triazinone 16 . Rates for interconversion at various temperatures were measured and an activation energy for the process determined. 相似文献
18.
A series of 3-substituted [1]benzothieno[3,2-d]pyrimidine derivatives has been synthesized as possible antileukemic agents by condensation of methyl 3-(ethoxymethylene)amino-2-benzothiophene carboxylate (II) with a variety of amines to afford the corresponding 3-aryl and 3-alkyl [I]benzothieno[3,2-d]pyrimidin-4(3H)-ones, Ill and IV, respectively. In addition, Mannich reactions of [I]benzothieno[3,2-d]pyrimidin-4(3H)-one (VIII) with formaldehyde and secondary amines gave the expected derivatives, IX. 3-Amino[I]benzothieno[3,2-d]-pyrimidin-4(3H)-one (VI) reacted with substituted aromatic aldehydes in the presence of boron trifluoride to yield the corresponding imines VII. 相似文献
19.
G. A. Reynolds J. A. Vanallan C. C. Petropoulos 《Journal of heterocyclic chemistry》1970,7(5):1061-1069
4-Dicyanomethylene-2-phenyl-4H-1-benzopyran (1) reacts with primary amines under mild conditions to give 4-imino-3-alkyl-5-alkylimino-2-phenyl-3,4-dihydro-5H-[1]benzopyrano[3,4-c]-pyridine derivatives which, in turn, are hydrolyzed with acid to 4-imino-3-alkyl-2-phenyl-3,4-dihydro-5H-[1]benzopyrano[3,4-c]pyridin-5-ones. When more vigorous conditions are employed for the reactions of 1 with primary amines, Dimroth rearrangements take place and the products are derivatives of 4-alkyl- (or aryl)amino-5-alkyl- (or aryl)imino-2-phenyl-5H-[1]benzopyrano-[3,4-c]pyridine. The latter compounds are hydrolyzed by acid to the corresponding 5-pyridone derivatives. The reaction of 1 with piperidine gives 2-phenyl-4-piperidyl-5H-[1]benzopyrano-[3,4-c]pyridin-5-one. Sodium methoxide reacts with 1 to give 3-cyano-2-methoxy-4-(2-hydroxyphenyl)-6-phenylpyridine. Two benzologs of 1 have been allowed to react with primary and secondary amines and the products are analogous to those obtained from 1 . 相似文献
20.
Peter Gajdoš Soňa Pavlíková Filip Bureš Alžbeta Krutošíková 《Central European Journal of Chemistry》2005,3(2):311-325
The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions
was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording
comparable yields. 相似文献