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1.
Zincated pyridazin-3(2H)-ones generated via bromine-magnesium exchange followed by transmetalation using ZnCl(2) or via lactam-directed ortho C4-H zincation with TMPZnCl·LiCl have been synthesized. These in situ created organometallics can be used in Negishi reactions with iodo(hetero)arenes delivering a new approach toward (hetero)arylpyridazin-3(2H)-ones. 相似文献
2.
Misbahul Ain Khan Maria Lucia De Brito Morley 《Journal of heterocyclic chemistry》1978,15(8):1399-1401
The diazotization of 3-aminocoumarin followed by its reduction gave the cournarin-3-yl-hydrazine which, without isolation, reacted with various carbonyl compounds in a Fisher's indohzation reaction to give derivatives (Ib-Ih) of the yet unreported system 3H,4H[1]benzopyrano[3,4-b]pyrrol-4-one. 相似文献
3.
Bernard Chantegrel Christian Deshayes Bernard Pujol Zhong Jia Wei 《Journal of heterocyclic chemistry》1990,27(4):927-934
The title compounds were prepared from ethyl 5-acyl- or 5-(1-hydroxyethenyl)isoxazole-4-carboxylates which in turn were prepared from ethyl 3-methylamino-2-butenoate or 3(2H)-furanones. 相似文献
4.
Nabih S. Girgis Roland K. Robins Howard B. Cottam 《Journal of heterocyclic chemistry》1990,27(7):1989-1991
Nucleosides of pyrrolo[2,3-d]pyridazin-4(5H)-ones were prepared by the single-phase sodium salt glycosylation of appropriately functionalized pyrrole precursors. The glycosylation of the sodium salt of ethyl 4,5-dichloro-2-formyl-1H-pyrrole-3-carboxylate ( 4 ), or its azomethino derivative 7 , with 1-bromo-2,3,5-tri-O-benzoyl-D-ribofuranose in acetonitrile afforded the corresponding substituted pyrrole nucleosides ethyl 4,5-dichloro-2-formyl-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrrole-3-carboxylate ( 5 ) and ethyl 4,5-dichloro-2-phenylazomethino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrrole-3-carboxylate ( 8 ), respectively. The latter, upon treatment with hydrazine, afforded the annulated product 2,3-dichloro-1-β-D-ribofuranosyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one ( 6 ), in good yield. The unsubstituted analog 1-β-D-ribofuranosyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one ( 9 ), was obtained upon catalytic dehalogenation of 6 . This report represents the first example of the synthesis of nucleosides of pyrrolopyridazines. 相似文献
5.
Muratov A. V. Eresko A. B. Tolkunov V. S. Tolkunov S. V. 《Russian Journal of Organic Chemistry》2019,55(3):345-350
Russian Journal of Organic Chemistry - A number of new 1-substituted 5,10-dihydro[1,2]diazepino[4,5-b]indole-4(3H)-ones were synthesized, and their structural modification was performed to obtain... 相似文献
6.
E. A. Sidorova E. S. Kostenko I. S. Arustamova E. A. Kaigorodova L. D. Konyushkin 《Chemistry of Heterocyclic Compounds》2011,47(3):294-301
The reactions of 2-aminonicotinamides with triethyl orthoformate, carboxylic acids chlorides, aldehydes, and 2-formylbenzoic
acid were studied. As a result pyrido[2,3-d]pyrimidin-4(1H)-ones, 2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-ones, and 5,7,11b,12-tetrahydropyrido[2',3':4,5]pyrimido- [2,1-a]isoindole-5,7-diones were obtained. 相似文献
7.
[reaction: see text] Novel and highly efficient syntheses of oxazolo[4,5-c]quinoline-4(5H)-ones (1) and thiazolo[4,5-c]quinoline-4(5H)-ones (2) from ethyl 2-chlorooxazole-4-carboxylate (4) and ethyl 2-bromo-5-chlorothiazole-4-carboxylate (13), respectively, are described. 相似文献
8.
1,3-Dipolar cycloadditions of diazoalkanes to pyridazin-3(2H)-ones 1–7 and pyridazin-3(2H)-thiones 8 and 9 are regioselective producing 3H -pyrazolo[3,4-d]pyridazin-4(5H)-ones 15–19, 27–29 and 34–38 as the major products. In some instances, the isomeric 3H-pyrazolo[3,4-d]pyridazin-7(6H)-ones, such as 20 and 23 were isolated as the minor products. From 3 and 6 the primary 3a,7a-dihydro cycloadducts 25 and 26 , and rearranged 1,2-dihydro intermediate 31 were isolated. From 10 and 1-diazoindane the isomeric exo- and endospiro products 39 and 40 were formed. 相似文献
9.
A series of two N-substituted-3(5)acyl4-ethoxycarbonyl-5(3)substituted isomeric pyrazoles underwent ring closure with hydrazine and methylhydrazine to give the new anticipated N(1)-or N(2)alkyl-3,7-disubstituted pyrazolopyridazin-4(5H)ones. The purpose of this study was to determine distinguishing criteria between the two isomers. From the comparative 1 H- and 1 3C-nmr spectra, sufficiently significant differences were observed. Uv and ir spectra showed no significant differences. 相似文献
10.
3:4-Fused furocoumarins and pyrrolocoumarins are synthesised from 3-hydroxy and 3-benzamido-substituted coumarins by a novel two step sequence. 相似文献
11.
Condensation of 2,3-diaminopyridine ( 1 ) with ethyl o-, m- and p-substituted benzoylpyruvates 2–9 gave two isomeric products. The preferential formation of one or the other isomer has been achieved by different reaction conditions. All the products appear to exist in the enamine form as evidenced by their 1H nmr and ir spectra. 相似文献
12.
M. Koóš 《Monatshefte für Chemie / Chemical Monthly》1994,125(8-9):1011-1016
Summary Sodium 2-aminothiophenoxide (1) reacts with ethyl 2-bromoalkanoates (2) under direct cyclization to form 2-alkyl-2H-1,4-benzothiazin-3(4H)-ones (3). Reaction of the sodium salt of 2-mercaptobenzimidazole (4) with2 or 2-bromoalkanoic acids (5) affords only S-alkylated products (6 or7, respectively). The cyclization products — 2-alkylbenzo[d]imidazolo[2,1-b]thiazolidin-3-ones (8) — can be obtained only from the corresponding 2-(2-benzimidazolylthio)alkanoic acids (7) by the action of acetic anhydride. Both compounds3 and8 exhibit only moderate antimicrobial activity against some gram-positive bacteria.
Synthese und antimikrobielle Wirkung von einigen 2-Alkyl-2H-1,4-benzothiazin-3(4H)-onen und 2-Alkylbenzo[d]imidazolo[2,1-b]thiazolidin-3-onen
Zusammenfassung Bei der Reaktion von Natrium-2-aminothiophenolat mit 2-Bromoalkansäure-ethylestern (2) entstehen als Cyclisierungsprodukte 2-Alkyl-2H-1,4-benzothiazin-3(4H)-one (3). Die Umsetzung von Natriumbenzimidazol-2-thiolat mit2 oder mit 2-Bromoalkansäuren (5) liefert nur S-Alkylierungsprodukte (6 oder7). Die Cyclisierungsprodukte — 2-Alkylbenzo[d]imidazolo[2,1-b]thiazolidin-3-one (8) — sind nur durch Umsetzung von entsprechenden 2-(2-Benzimidazolylthio)-alkansäuren (7) mit Acetanhydrid erhältlich. Die Verbindungen3 und8 weisen nur mäßige antimikrobielle Wirkung gegen einige gram-positive Bakterien aus.相似文献
13.
Present in a number of small molecule derivatives that display a wide range of biological activities, the dihydropyrrolo[3,4-b]indol-(2H)-one (DHPI) core represents an underexplored heterocyclic scaffold. Given the pharmaceutical potential of the DHPI motif, the development of synthetic methodologies that permit their expedient assembly would be highly desirable. Herein, we describe a novel strategy for the construction of the DHPI core from 3-iodo-1H-indolyl substrates, employing an unprecedented Pd-catalyzed intramolecular aminocarbonylative ring closure. The compatibility of our optimized protocol with various functional groups is highlighted through the synthesis of a range of diversely substituted DHPI derivatives in up to 90 % isolated yield. 相似文献
14.
V. P. Kruglenko 《Chemistry of Heterocyclic Compounds》2001,37(4):500-503
The reactions of substituted 5H-imidazo[1,2-b]-1,2,4-triazepin-4-ones and -thiones with bromine and N-bromosuccinimide have been studied. Derivatives of 3- and 8-bromo-, 3,8-dibromoimidazo[1,2-b]-1,2,4-triazepine and 5H-2-bromomethyl-3-methyl-7,8-diphenylimidazo[1,2-b]-1,2,4-triazepin-4-one are formed, depending on the degree of substitution, the nature of the brominating agent, and the reaction conditions. 相似文献
15.
Aillaud I Bossharth E Conreaux D Desbordes P Monteiro N Balme G 《Organic letters》2006,8(6):1113-1116
[reaction: see text] N-Methyl-4-alkoxy-3-alkynylpyridin-2(1H)-ones readily undergo iodine-promoted 5-endo-heteroannulation under mild conditions to 3-iodofuropyridinium triiodide salts in moderate to good yields. The latter may be dealkylated in situ upon exposure to an iodide anion to provide the corresponding 3-iodofuro[2,3-b]pyridin-4(1H)-ones. The same strategy applies to the formation of furo[2,3-b]quinolin-4(9H)-ones. 相似文献
16.
Kenji Kaji Hiromu Nagashima Yusho Ohta Keizo Tabashi Hirohisa Oda 《Journal of heterocyclic chemistry》1984,21(5):1249-1255
The synthesis of 1,3-disubstituted and 1,3,5-trisubstituted 1H-pyrazolo[3,4-d]pyridazin-4(5H)-ones is conveniently performed by photochemical cyclization. Functionalization of the former compounds leading to the formation of 1,4-disubstituted and 1,3,4-trisubstituted 1H-pyrazolo[3,4-d]pyridazines is smoothly effected through pertinent nucleophilic substitutions. 相似文献
17.
本文利用2-氨基喹啉和2-氨基苯骈咪唑作为亲核试剂,与5-(双甲硫基亚甲基)丙二酸亚异丙酯(1)、5-(甲硫基亚烃基)丙二酸亚异丙酯(3)反应,开发出3-取代-(1H)-嘧啶-[1,2-a]喹啉-1-酮(5)和2-取代嘧啶[1,2-a]苯骈咪唑-4-(10H)-酮(6)通用的简便合成法。 相似文献
18.
R. Richard L. Hamer Richard C. Effland Joseph T. Klein Francis P. Huger Jeffrey C. Wilker 《Journal of heterocyclic chemistry》1988,25(2):517-521
The synthesis of a series of 5-phenylpyrrolo[1,2-b][1,2,5]triazepin-2(3H)-ones 1 as potential anxiolytic agents is described. Benzoylation of 1-phthalimidopyrrole, followed by hydrolysis, gave the 1-amino-2-benzoylpyrroles 3 . These were further functionalized to give the penultimate 1-aminoacetamido-2-benzoylpyrroles 8 and 9 , which were cyclized to the target pyrrolotriazepines 1. 相似文献
19.
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