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1.
Roberto Martínez Corte C. Eduardo Salazar E. Olivia Linzaga E. Irma 《Journal of heterocyclic chemistry》1994,31(4):1061-1063
Catalytic hydrogenation of o-nitrophenylbenz[a], benz[c], dibenz[a,h] and dibenz[a,g]acridinones using Pd/C as catalyst, at 60 psi of pressure, gave the hiterto unknown benzoquinoacridine N-oxides and benzo-pyranonaphthyridine N-oxides. The structure of all products was corroborated by ir, 1H- and 13C-nmr and mass spectra data. 相似文献
2.
N. E. Golantsov A. V. Karchava V. M. Nosova M. A. Yurovskaya 《Russian Chemical Bulletin》2005,54(1):226-230
4-Substituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles were synthesized from 2-cyanoindole. (R)-4-Methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole was obtained by the Mitsunobu reaction. Stereoselective reduction of 4-substituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles gave 4-substituted 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles. (4R, 10aR)-4-Methyl-1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indole was synthesized.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 221–225, January, 2005. 相似文献
3.
Reactions of ketene dithioacetals, 1-[1-substituted 2,2-bis(methylthio)ethenyl]pyridinium 1a-i or -isoquinolinium 2a,b iodides with aromatic N-imines, 1-aminopyridinium 3a-1,1 -aminoquinolinium ( 4 ), and 2-amino-isoquinolinium ( 5 ) mesitylene sulfonates gave the corresponding 2-methylthioimidazo[1,2-a]pyridines 9a-k , 2-methylthiopyrazolo[1,5-a]pyridines 11a-q , 2-methylthioimidazo[2,1-a]isoquinoline derivatives 10a,b and 2-methylthiopyrazolo[1,5-a]quinoline ( 12 ). The benzoyl compounds, 1-[1-benzoyl-2,2-bis(methylthio)ethenyl]-pyridinium iodides 1g,h,i reacted with N-imine 3a to give the 3-benzoyl-2-methylthioimidazo[1,2-a]pyridines 9h-k . The reaction of pyridinium ketene dithioacetals 1a,f,g (R1 = COOEt, COPh, and CN) with substituted pyridinium N-imines having an electron-withdrawing group on the pyridine ring afforded only the corresponding pyrazolo[1,5-a]pyridine derivatives 11j-r in good yields. Reactions of ketene dithioacetals with various S-imines are also described. Possible mechanisms for the formation of 9 and 11 are described. 相似文献
4.
Norton P. Peet James Malecha Michael E. Letourneau Shyam Sunder 《Journal of heterocyclic chemistry》1989,26(1):257-264
New methodology is described for the construction of tricyclic heterocycles. Thus, a double displacement reaction of l-(2-fluorobenzoyl)-2-methylthio-2-imidazoline ( 8a ) with 1,1-dialkylhydrazines gave 10-substituted 2,10-dihydroimidazo[2,1-b]quinazolin-5(3H)-ones in good yield. The corresponding 1-(2-nitrobenzoyl)-2-meth-ylthio-2-imidazolines also underwent double displacement reactions with hydrazines. Other tricyclics made using double displacement reactions were pyrimido[2,1-b]quinazolines, imidazo[1,2-a]pyrido[2,3-d]pyrimidines, and imidazo[1,2-a]pyrazolo[3,4-d]pyrimidines. Treatment of 8a with hydrazine hydrate or methylhydrazine gave products resulting from displacement, but did not afford fused benzotriazepinones. 相似文献
5.
Kaname Takagi Tomoji Aotsuka And Hikari Morita Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1986,23(5):1443-1449
Reactions of 4-ethoxycarbonylamino-1H-1,5-benzodiazepine-3-carbonitrile (2) with aliphatic primary amines gave 1-substituted 4-(2-aminoanilino)pyrimidin-2(1H)-one-5-carbonitriles 3. Analogous reactions of 2 with aromatic primary amines afforded 2-(2′-anilino-1′-cyanovinyl)benzimidazoles 5 and 6. Upon treatment with triethylamine, 3 underwent intramolecular cyclization to give 3-substituted 5-aminopyrimidino[4,5-b]-[1,5]benzodiazepin-2(3H,11H)-ones 8 . Heating of 3 with p-toluenesulfonic acid in ethanol gave 2-substituted pyrimidino[1,6-a]benzimidazol-1(2H)one-4-carbonitriles 9 . Reactions of 2 with hydrazines were also described. Mechanistic pathways are proposed to account for the products. 相似文献
6.
5-Halovalerophenones reacted with substituted thiosemicarbazides affording two different heterocyclic ring systems. Reactions with 4-substituted thiosemicarbazides gave 3-aryl-4,5,6,7-tetrahydro-1H-1,2-diazepine-1-carbothioamides whereas reactions with 2,4-dimethylthiosemicarbazide gave hexahydro-1,3-dimethyl-8a-aryl[1,2,4]triazolo[1,5-a]pyridine-2(3H)-thiones. 相似文献
7.
Noritoshi Ishida Kimiaki Imafuku Teruo Kurihara 《Journal of heterocyclic chemistry》1992,29(5):1219-1224
The reactions of 4-amino-2-phenylcycloheptimidazole with alkyl iodides and α-bromoketones gave respectively 1-alkyl- and 1-acetonyl- (or 1-phenacyl)-substituted cycloheptimidazol-4(1H)-ones, while the reactions with acyl chlorides gave 4-arylamino-2-phenylcycloheptimidazoles. On the other hand, 2,4-diaminocycloheptimidazole were benzoylated with benzoyl chloride on the amino group at the 2- and/or 4-position and reacted with α-haloketones to give tricyclic 2-substituted 9-aminocyclohept[d]imidazo[1,2-a]imidazoles. 相似文献
8.
Three-component condensation of 2-aminobenzimidazole and its N-substituted derivatives with formaldehyde and primary amines gave 1,2,3,4-tetrahydro[1,3,5]triazino[1,2-a]benzimidazoles.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 355–356, February, 2007. 相似文献
9.
Syntheses and Investigations of [Oxazolo[2,3-a]isoindol-9b(2H)-yl]phosphonates and -phosphinates: a New Class of Heterocycles We attempted to synthesize diethyl (1-methyl-2-phthalimidoethyl)phosphonate ( 14a ) in a Michaelis-Becker reaction using diethyl sodiophosphonate ( 13 ) and the tosylate 12a of (2-hydroxypropyl)phthalimide as starting materials. Instead of TsO substitution in 12a by the nucleophile 13 , the carbonyl C-atom of the phthalimido moiety was attacked by 13 , followed by an intramolecular nucleophilic substitution at C(2) of the side chain leading to the (oxazolo[2,3-a]isoindolyl)phosphonate 15a (Scheme 1). Similarly, 12a and N-(2-bromoethyl)phthalimide ( 12b ) reacted with butyl (benzene)sodiophosphinate ( 18 ) to the (oxazolo[2,3-a]isoindolyl)(phenyl)phosphinates 20a and 20b , respectively (Scheme 2). The attempt to synthesize enantiomerically pure 2-substituted (2-phthalimidoethyl)phosphonates 27 starting from L -α-amino-acids failed, too (Scheme 3): the main products of the reaction of the N,N-phthaloyl-O1-tosyl-L -aminoalcohols 25a–d with 13 were the 3-substituted (oxazolo[2,3-a]isoindolyl)-phosphonates 26a–d , the desired 27b and 27c being observed as by-products in the 31P-NMR spectrum. 相似文献
10.
利用3-甲硫基-4-乙氧羰基-5-氨基-1H-吡唑分别与甲基/芳基烯胺酮反应, 合成了8种新的化合物2-甲硫基-7-取代-3-吡唑并[1,5-a]嘧啶甲酸乙酯(3a~3g)和2-甲硫基-5-甲基-3-吡唑并[1,5-a]嘧啶甲酸乙酯(4a). 化合物的结构均经元素分析, IR, 1H NMR, MS所证实, 异构体3a和4a的结构进一步由13C NMR, HMQC和HMBC确认. 同时, 探讨了区域选择性合成吡唑并[1,5-a]嘧啶类化合物可能的反应机理, 并对部分化合物杀菌活性进行了测试. 相似文献
11.
A. Monge Vega I. Aldana M. M. Rabbani E. Fernandez-Alvarez 《Journal of heterocyclic chemistry》1980,17(1):77-80
This paper describes the synthesis of the previously unknown 11H-1,2,4-triazolo[4,3-b]pyridazino[4,5-b]indoles (2) and 11H-tetrazolo[4,5-b]pyridazino[4,5-b]indoles (3) from 4-hydrazino-5H-pyridazino[4,5-b]indoles (1) , as well as the synthesis of 1,2,4-triazolo[3,4-f]-1,2,4-triazino-[4,5-a]indoles (10) from 2-indolecarbohydrazide (4) . Compounds 2 were obtained by acylation of compounds 1 , followed of thermal cyclization and compounds 3 by treating compounds 1 with nitrous acid. The reactions of compound 4 with formic acid or ethyl orthoformiate gave 1,2-dihydro-1-oxo-1,2,4-triazino[4,5-a]indole (6) . Treating this last compound with phosphorus oxychloride or phosphorus pentasulfide, followed by hydrazine, gave 1-hydrazino-1,2,4-triazino-[4,5-a]indole (9) . Acylation of this last compound, followed of cyclization gave compounds 10 . All the compounds were characterized by elemental analysis and ir and 1H-nmr spectra. 相似文献
12.
A synthesis of the 4,5-dihydro derivatives of the previously known pyrazolo[3,4-a]acridine ring system is described. The reaction of a 3,4-dihydroacridin-1(2H)-one with N,N-dimethylformamide dimethyl acetal gave a reactive enamino ketone, which yielded the desired heterocycle upon reaction with hydrazine. Using this chemistry, 11-amino-4,5-dihydro-2H-pyrazolo[3,4-a)acridine ( 3 ) and a number of its 2-substituted derivatives 4a-k were synthesized and evaluated as acetylcholinesterase inhibitors, based on their relationship to 1,2,3,4-tetrahydro-9-acridinamine (THA). 1-Amino-4,5-dihydro-1H-pyrazolo[3,4-a]acridine ( 11a ) and 2-amino-4,5-dihydro-1H-pyrazolo[3,4-a]acridine ( 11b ) were also synthesized and investigated as potential cholinesterase inhibitors. 相似文献
13.
Deprotonation, methylation, and air oxidation of polycyclic arenes coordinated to chromium(0), (η6-arene)Cr(CO)3, produced ring-methylated products with high selectivity and in good yield. This procedure gave 3-methylbenz[a]anthracene from (η6-benz[a]anthracene)Cr(CO)3, 3-methylphenanthrene from (η6-phenanthrene)Cr(CO)3, 2-acetyl-6-methylphenanthrene from (η6?2-acetylphenanthrene)Cr(CO)3, and 3,7,12-trimethylbenz[a]anthracene from (η6?7,12-dimethylbenz[a]anthracene)Cr(CO)3. 相似文献
14.
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
15.
A series of 3-substituted aminoimidazo[1,5-a]pyridine derivatives have been synthesized by cyclodesulfurization of a variety of N′-substituted-N-(2-pyridylmethyl)thioureas with dicyclohexylcarbodiimide (DCCD). 1H Nmr spectral analysis of all synthesized compounds is given. 相似文献
16.
Irene Ortín 《Tetrahedron》2009,65(11):2201-6277
N-Acyliminium cyclization of 6-substituted (3R∗,6R∗,11aS∗)-3-arylmethyl-pyrazino[1,2-b]isoquinoline-1,4-diones gave with very good yields a novel tetrahydroisoquinoline pentacyclic core framework (29), while this reaction failed in all-cis-isomers to give instead conjugated enamines by deprotonation. Electronic and steric factors that govern the approach to both diastereomers from 6-substituted pyrazino[1,2-b]isoquinoline-1,4-diones have been studied. 相似文献
17.
Yu. M. Volovenko G. G. Dubnina A. N. Chernega 《Chemistry of Heterocyclic Compounds》2004,40(1):94-100
Reactions of 3,4-dichloro-N-R-maleimides with substituted thiouracils at 40°C gave a 1:1 mixture of isomers of pyrrolothiazolopyrimidinetriones. Under conditions of thermodynamic control (100°C, 5 h) only pyrrolo[3',4':4,5]thiazolo[3,2-a]pyrimidine-4,6,8-triones were formed, hydrolysis of which followed by decarboxylation gave 5-oxo-5H-thiazolo[3,2-a]pyrimidine-2-carboxamide. The structure of N2-phenyl-6-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-2-carboxamide was confirmed by X-ray crystallography. Analogous cyclization of 3,4-dichloro-N-R-maleimides with 2-thioxoquinazol-4-one also gave a mixture of two isomers which were successfully separated by fractional crystallization. 相似文献
18.
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
19.
Edwige Jeanneau-Nicolle Claude Bosso Martine Benoit-Guyod Grard Leclerc 《Journal of mass spectrometry : JMS》1993,28(1):37-41
The electron impact mass spectra of two series of 5-oxo-tetrahydro-5H-thiazolo [3,2-a]pyrimidine-6-ethylcarboxylates and 7-oxo-tetrahydro-7H-thiazolo [3,2-a]pyrimidine-6-ethylcarboxylates were measured and fragmentation patterns examined. Structures were assigned from analysis of oxo molecular ion fragmentations. Compounds of the 5-oxo series gave an [M – CO2C2H5]+ fragmentation whereas compounds of the 7-oxo series gave three characteristic cleavages. This decomposition was confirmed for one pair of isomers by high-resolution mass spectrometry and unimolecular mass-analysed ion kinetic energy spectrometry. Electron impact mass spectrometry is a convenient method for assigning structures of 5- and 7-oxo regioisomers of tetrahydrothiazolo[3,2-a]pyrimidine-6-carboxylates. 相似文献
20.
Emile Bisagni Alain Civier Jean-Pierre Marquet 《Journal of heterocyclic chemistry》1975,12(3):461-465
Treatment of 4-hydroxy-6-methylpyran-2-one with chloracetalhyde in basic aqueous medium gave 6-methylfuro[3,2-c]pyran-4-one. This compound reacted with ammonium hydroxide and some primary amines to form the corresponding N-substituted furo[3,2-c]pyrid-4-ones which may also be obtained from 4-hydroxy-α-pyridones. Furo[3,2-c]pyran-4-one was acylated at the 2 position and 4-chloro-6-methylfuro[3,2-c]pyridine easily gave 4-substituted derivatives by displacement of the halogen atom. 相似文献