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1.
Reaction of 2-substituted-5-aroyl-3(2H)-isothiazolones 1 with phenylhydrazine in refluxing ethanol was found to give sulfur-free products, which were characterized as 3-phenylhydrazono-3-aroyl-N-substituted-pro-pionamides 4. Acid hydrolysis of the 3-benzoyl compounds 4 was shown to yield 1-phenyl-3-benzoyl-2-pyrazolin-5-one ( 7 ), whose structure was confirmed by an independent synthesis starting with the chloride of 1-phenyl-5-methoxypyrazole-3-carboxylic acid ( 10 ). 相似文献
2.
Reaction of N-substituted amides of 2-chloro- or 4-chloronicotinic acid with CH-acidic nitriles in the presence of a base provides a convenient access to amino derivatives of 1,6-naphthyrid-5(6H)-one, compounds of type 4 and 5 , or 2,7-naphthyrid-1(2H)-one 7. 相似文献
3.
Norbert Klempier Anna De Raadt Herfried Griengl Gottfried Heinisch 《Journal of heterocyclic chemistry》1992,29(1):93-95
Chemoselective hydrolysis of heterocyclic nitriles can be achieved by an easy to use immobilized biocatalyst prepared from Rhodococcus sp. Pyrimidine-2-carbonitrile ( 2a ) and 3-chloropyridazine-4-carbonitrile ( 4a ) were converted into the corresponding amides while from 2-ethoxycarbonyl-4-pyridinecarbonitrile ( 1a ), 6-methylpyridazine-3-carbonitrile ( 3a ), 3-chloropyridazine-4-carbonitrile ( 4a ), 3-ethoxycarbonyl-4,5-dihydroisoxazole-5-carbonitrile ( 8a ), indole-3-carbonitrile ( 9a ) and indole-3-ylacetonitrile ( 10a ) the acids were formed. 相似文献
4.
Hassan Attia Elfahham Fathy Mohamed Abdel-Galil Yusria Rizk Ibraheim Mohamed Hilmy Elnagdi 《Journal of heterocyclic chemistry》1983,20(3):667-670
Several new pyrazolo[1,5-a]pyrimidines and pyrano[2,3-c]pyrazoles were synthesized viathe reaction of the cinnamonitrile derivatives 1a-c with 5-amino-3-phenylpyrazole ( 1 ), 3-amino-2-pyrazolin-5-one ( 2 ) and 3-amino-1-phenyl-2-pyrazolin-5-one ( 22 ). 相似文献
5.
Wu-Yun Ren Kambhampati V. B. Rao Robert S. Klein 《Journal of heterocyclic chemistry》1986,23(6):1757-1763
Several novel 2,4,6-trisubstituted thieno[3,2-d]pyrimidines were synthesized from the hitherto unknown 3-amino-5-methyl-(or 5-phenyl)thiophene-2-carbonitriles 7 and 8 . o-Aminonitriles 7 and 8 were obtained in a single step by conjugate addition of mercaptoacetonitrile (generated in situ) to substituted acetylenic nitriles 4 and 5 and annelation of the intermediate vinylic thioethers. 相似文献
6.
The o-quinoid 8π electron system 2 , generated by thermal ring opening of benzothiete ( 1 ), enters regio-specific [8π + 2π] cycloaddition reactions with electron-deficient nitriles 3a-d , yielding the 4H-1,3-benzothiazines 4a-d. A competitive dimerization of 1 leads to 1,5-dibenzo[b,f]dithiocin (5). Depending on the nitrile further competitive or subsequent reactions (2 + 3b → 7b, 2 + 3d → 4d → 8d) can occur. The cycloadducts 10e and 11e gained from 3e anticipate a primary cleavage of 3e to methylisothiocyanate 9e which reacts at the C?N double bond as well as at the C?S double bond. 相似文献
7.
An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH4OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling. 相似文献
8.
The heterocyclization of unsaturated nitriles and ethyne catalyzed by cyclopentadienyl-1,5-cis,cis-cyclooctadiene-cobalt(I) and promoted by light has been studied in toluene as solvent. Acrylonitrile and substituted acrylonitriles gave results of interest in the preparation of 2-vinylpyridines. No reaction could be observed using fumaronitrile, maleonitrile or allyl cyanide. The (E)/(Z)-ratio of educts and products seems to be not influenced by conditions in the reaction. 相似文献
9.
V. N. Yarovenko M. M. Krayushkin O. V. Lysenko L. M. Kustov I. V. Zavarzin 《Russian Chemical Bulletin》1994,43(3):402-404
A new synthetic method for the preparation of15N-labeled nitriles from nonlabeled nitriles is proposed.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 444–446, March, 1994. 相似文献
10.
K. G. Dave C. J. Shishoo M. B. Devani R. Kalyanaraman S. Ananthan G. V. Ullas V. S. Bhadti 《Journal of heterocyclic chemistry》1980,17(7):1497-1500
Nitriles are known to give rise to salts of different compositions with halogen acids. Many of the reactions undergone by nitriles under the influence of halogen acids are, in many cases, assumed to proceed via the intermediate formation of highly reactive imidoyl derivatives. The intermediates produced, in situ, by the reaction of nitriles with hydrogen chloride should, in principle, be capable of reacting with compounds containing appropriately placed nucleophilic and electrophilic centers leading to the formation of a heterocycle incorporating the C=N of the nitrile. Thus, the reaction of aliphatic, aromatic and heterocyclic nitriles with a variety of ortho aminocarbonyl derivatives such as nitriles, amides, esters and ketones of benzene, thiophen, furan, pyrrole, benzothiophene and pyridothiophene have been found to yield the corresponding condensed pyrimidines in fair to good yields. This constitutes a facile and versatile one-pot synthesis of condensed pyrimidines. 相似文献
11.
Summary An effective catalyst for the conversion of isoalkanols into nitriles under the action of ammonia is pure zinc oxide at 390°. In presence of zinc oxide at this temperature, isobutyl alcohol reacts with ammonia with formation of isobutyronitrile in yields of up to 76.6% and isopentyl alcohol gives isovaleronitrile under the same conditions in yields of up to 71.4%. 相似文献
12.
The reaction of fluorinated ylide-anions, generated from nucleophilic addition of organolithium compounds to perfluoroacylcyanomethyl enetriphenylphosphoranes 1, with iodine or 1,2-diiodoethane afforded perfluoroalkylated a-iodo-a,b-unsaturated nitriles in 70–97% yields. Keywords: Fluorinated phosphorane; Synthesis; Perfluoroalkylated α-iodo-α,β-unsaturated nitriles; NMR spectroscopy; IR spectroscopy; Mass spectrometry 相似文献
13.
Roberto Ballini Dennis FioriniMaria Victoria Gil Alessandro Palmieri 《Tetrahedron letters》2003,44(50):9033-9034
The reaction of nitroalkanes with 2-chloro-3-phenylsulfonylpropanenitrile, in the presence of three equivalents of DBU at −10°C, allows the synthesis of polyfunctionalized α,β-unsaturated nitriles. The method proceeds through three different reactions carried out in a tandem sequence, allowing the one-pot formation of the α,β-unsaturated nitriles, generally, with complete E stereochemistry. 相似文献
14.
Nishiwaki N Kobiro K Hirao S Sawayama J Saigo K Ise Y Okajima Y Ariga M 《Organic & biomolecular chemistry》2011,9(19):6750-6754
A carbamoyl-substituted nitrile oxide was generated upon treatment of easily available 2-methyl-4-nitro-3-isoxazolin-5(2H)-one with THF (not dried); the reaction proceeded efficiently even in the absence of any special reagents and reaction conditions. The nitrile oxide caused 1,3-dipolar cycloaddition with common aliphatic nitriles or electron-rich aromatic nitriles to afford 3-functionalized 1,2,4-oxadiazoles, which are expected to serve as precursors for the preparation of a variety of functional materials by the chemical transformation of the carbamoyl group. While conventional preparative methods for 1,2,4-oxadiazoles involve the cycloaddition of an electron-rich nitrile oxide with an electron-deficient nitrile or a nitrile activated by a Lewis acid, our method employs the complementary combination of an electron-rich nitrile and an electron-deficient nitrile oxide- the inverse electron-demand 1,3-cycloaddition. The DFT calculations using B3LYP 6-31G* supported the abovementioned inverse reactivity, and also suggested the presence of an accelerating effect by the carbamoyl group as a result of hydrogen bond formation with a dipolarophilic nitrile. 相似文献
15.
A. L. Lapidus M. V. Tsapkina E. A. Kravtsova E. G. Gorlov 《Russian Chemical Bulletin》1997,46(8):1476-1478
The promoting effect of potassium included in Cr/MgO catalysts for the synthesis of nitriles from acetonitrile and methanol
was found. The 5% Cr-0.5% K/MgO catalyst exhibited the highest activity in the synthesis of nitriles.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1540–1542, August, 1997. 相似文献
16.
Ichizo Okabayashi 《Journal of heterocyclic chemistry》1980,17(6):1339-1339
2,4-Dihydro-5-methyl-2-phenyl-4-(9H-xanthen-9-yl)-3H-pyrazol-3-one ( 3 ) was prepared by the condensation of phenylhydrazine and ethyl α-acetyl-9H-xanthene-9-acetate ( 2 ), or 9H-xanthen-9-ol ( 1 ) and 2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one ( 4 ). 5-Amino-2,4-dihydro-2-phenyl-4-(9H-xanthen-9-yl)-3H-pyrazol-3-one ( 6 ) was obtained by the condensation of 1 and 5-amino-2,4-dihydro-2-phenyl-3H-pyrazol-3-one ( 5 ). 相似文献
17.
A metal-free catalytic method for the conversion of aromatic and aliphatic aldoximes to nitriles at room temperature using oxalyl chloride (1.2 equiv) in combination with 5 mol % of triphenylphosphine oxide is reported. Of the many potential pathways leading from oxime to nitrile a manifold involving chlorophosphonium salt-catalysed decomposition of oxime chlorooxalates formed in situ is shown to be operative. 相似文献
18.
The cheap, commercially available iron complex, Fe(NO3)3·9H2O, has been used to catalyse the formation of amides by the addition of amines to nitriles. 相似文献
19.
V. P. Kislyi E. B. Danilova V. V. Semenov A. A. Yakovenko F. M. Dolgushin 《Russian Chemical Bulletin》2006,55(10):1840-1847
Base-catalyzed cyclization of O-alkylated α-hydroxyimino nitriles gave mixtures of 4-aminoisoxazoles and 5-aminooxazoles, their ratio depending on the substituent
structures and the reaction conditions. The formation mechanism of 5-aminooxazoles in this reaction is discussed.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1773–1780, October, 2006. 相似文献
20.
Rogelio P. Frutos Isabelle Gallou Diana Reeves Yibo Xu Dhileepkumar Krishnamurthy Chris H. Senanayake 《Tetrahedron letters》2005,46(48):8369-8372
Expedient and practical new methodology for the synthesis of substituted imidazoles was developed to provide a rapid access to a variety of 2-substituted, 1,2-disubstituted and 1,2,4-trisubstituted imidazoles by the direct CuCl-mediated reaction of nitriles with α-amino acetals in an intermolecular as well as intramolecular fashion. 相似文献