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1.
Condensation of pyridinium N-alkyl-, N-cycloalkyl-, N-benzyl-, and N-phenethylcarb-amoylmethylenides with ethyl arylidenecyanoacetates stereoselectively gives 4,5-trans-1-alkyl-, 4,5-trans-l-cycloalkyl-, 4,5- trans-1-benzyl-, and 4,5-trans-1-phenethyl-4-aryl-3-cyano-6-oxo-5-(3-R-1-pyridinio)-1,4,5,6-tetrahydropyridin-2-olates. However, pyridinium N-arylcarb-amoylmethylenides react with the same esters without ring closure, yielding Michael adducts, viz., ethyl 3-aryl-4-(N-arylcarbamoyl)-2-cyano-4-(1-pyridinio)butyrates. 相似文献
2.
Shainyan B. A. Nindakova L. O. Ustinov M. V. Chipanina N. N. Sherstyannikova L. V. 《Russian Journal of Organic Chemistry》2002,38(12):1802-1805
The reaction of sodium diphenylamide with 2,2-dimethyl-4,5-bis(tosyloxymethyl)-1,3-dioxolane gave (+)-(4S,5S)-2,2-dimethyl-4,5-bis(diphenylaminomethyl)-1,3-dioxolane, which was brought into complex formation with cobalt chloride. Treatment of 2,2-dimethyl-4,5-bis(tosyloxymethyl)-1,3-dioxolane with sodium N-methylanilide resulted in cleavage of the SÄO bond in the p-toluenesulfonate moiety with formation of N-methyl-N-phenyl-p-toluenesulfonamide and 4,5-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane disodium salt. Diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate reacted with methylamine to give the corresponding dicarboxamide which was reduced with lithium aluminum hydride to (4S,5S)-2,2-dimethyl-4,5-bis(methylaminomethyl)-1,3-dioxolane having chiral carbon and nitrogen atoms. 相似文献
3.
Reduction of 4,5-dimethoxy-2-carbomethoxymethylbenzenesulfonyl chloride and 4,5-dimeth-oxy-2-carboethoxyethylbenzenesulfonyl chloride with zinc, hydrochloric acid, produced the corresponding o-mercapto-aeids which then cyclized to thiaindanone and thiochromanone, respectively. Thiaindanone and thiochromanone reacted readily with aniline to give 4,5-dimeth-oxy-2-mereaptophenyl-N-phenylacetamide and 4,5-dimethoxy-2-mercaptophenyl-N-phenylpropyl-amide. Mercaptophenyl N-phenylacetamide yielded in two steps the 4,5-dimethoxy-2-N-phenyl-acetarnido(3′,4′ -dimethoxyphenylthio)benzene, which was cyclized to the 2,3,7,8-tetramethoxy-10,11-dihydrodibenzo[b, f]thiepin-10-one. Reduction of thiepinone with sodium borohydride leads to the corresponding alcohol. 相似文献
4.
A number of new and interesting 2-amino-4-(N-substituted)imino-4,5-dihydrothiazoles were synthesized by reacting thiourea (or thiourea hydrochloride) with N-alkyl- or N,N-dialkyl-N′-p-toluenesulfonyl-α-chloroacetamidines, where the N,N-alkyl groups were ethyl, cyclohexyl, benzyl, β-phenethyl, (3,5-dimethyl-1-adamantyl)-methyl, as well as N,N-dimethyl- and N,N-pentamethylene. Reactions of N-alkyl-N-p-toluenesulfonyl-2-chloroacetamidines (substituents being N-ethyl, N-benzyl and N,N-dimethyl) with thiourea hydrochloride in hot 2-propanol furnished 2-amino-4-(p-toluenesulfonyl)imino-4,5-dihydrothiazole (in 51, 60 and 65% yields, respectively) and the corresponding amine hydrochloride. In hot acetone or butanone, the reactions of these N-sulfonyl-2-chloroacetamidines with excess thiourea provided 2-amino-4-N-(alkyl or N,N-dialkyl)imminium-4,5-dihydrothiazole chlorides in 25–80% yield. The by-product from these reactions was p-toluenesulfonamide. The structures of the products were established by chemical transformations and spectral methods (nmr and mass spectra). 相似文献
5.
Bobrov A. V. Averkiev B. B. Zlotin S. G. Antipin M. Yu. 《Russian Chemical Bulletin》2001,50(7):1287-1290
The reaction of 3,7-dichlorobisisothiazolo[4,5-b:4",5"-e]pyrazine with MeONa in MeOH afforded 3-chloro-5,6-dimethoxyisothiazolo[4,5-b]pyrazine. The reactions of the former with benzylamine, morpholine, and aniline gave rise to the corresponding N,N"-bis(5-amino-3-chloroisothiazol-4-yl)diazenes. In the case of benzylamine, 3,7-bis(benzylamino)bisisothiazolo[4,5-b:4",5"-e]pyrazine was isolated as a by-product. The crystal structure of N,N"-bis(5-benzylamino-3-chloroisothiazol-4-yl)diazene was established by X-ray diffraction analysis. 相似文献
6.
Darrcll E. O'Brien Louis T. Weinslock C. C. Cheng 《Journal of heterocyclic chemistry》1970,7(1):99-105
Condensation of substituted anthranilaldehydes with barbituric acid results in the formation of 2,4-dioxopyrimido[4,5-b]quinolines. Using this general synthetic approach, 7,8-dimethyl-2,4-dioxo-10-ribityl-2,3,4,10-tetrahydropyrimido[4,5-b]quinoline (10-deazariboflavin) was prepared by the condensation of barbituric acid with 4,5-dimethyl-N-ribitylanthranilaldehyde. The latter was obtained in situ by the treatment of 1-[4,5-dimethyl-N-(ribityl)anthraniloyl]-2-(p-toluenesulfonyl)hydrazine, prepared from 4,5-dimethylanthranilic acid with anhydrous sodium carbonate. 相似文献
7.
Gazieva G. A. Baranov V. V. Kravchenko A. N. Makhova N. N. 《Russian Journal of Organic Chemistry》2011,47(10):1572-1575
Reactions of N-(hydroxyalkyl)ureas with 4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones gave previously unknown 4,6-dialkyl-1-hydroxyalkyl-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-2-ones which may be regarded as thio analogs of N-(hydroxyalkyl)glycolurils. 相似文献
8.
V. I. Ovcharenko O. N. Chupakhin I. S. Kovalev E. V. Tretyakov G. V. Romanenko D. V. Stass 《Russian Chemical Bulletin》2008,57(10):2227-2229
The SNH reaction of lithiated 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-1-oxyl 3-oxide with quinoline N-oxide affords 4,4,5,5-tetramethyl-2-(1-oxidoquinolin-2-yl)-4,5-dihydro-1H-imidazole-1-oxyl 3-oxide. 相似文献
9.
Franciszek Saczewski Anita Bulakowska Maria Gdaniec 《Journal of heterocyclic chemistry》2002,39(5):911-915
The ureidation reactions of 2‐ and 4‐picoline N‐oxides with 2‐chloro‐4,5‐dihydroimidazole are described. A mechanism of novel thioureidation reaction of 4‐picoline N‐oxide with 2‐(4,5‐dihydro‐1H‐imidazol‐2‐ylthioxy)‐4,5‐dihydro‐1H‐imidazole is proposed. Structural assignment is confirmed by 1H and 13C nmr as well as by X‐ray crystallography. 相似文献
10.
Max Robba Jean-Charles Lancelot Daniel Maume Alain Rabaron 《Journal of heterocyclic chemistry》1978,15(7):1159-1163
1,2,4-Triazino[4,5-b]indazol-1(2H)one and its derivatives were prepared by transposition of 3-[2-(-1,3,4-oxadiazolyl)]indazole or by ring closure of indazole ethoxymethylidenehydrazides. The synthesis of 1,2,3,4-tetrahydro-l,2,4-triazino[4,5-b]indazole-1,4-dione was achieved by cyclising the N-carbethoxyhydrazide of indazole-3-carboxylic acid and the synthesis of 1,2,4-triazino-[4,5-b]indazol-4(3H)one was made by cyclising the N-carbethoxy-hydrazone of indazole-3-carboxaldehyde. The Oxydation of 1,2,4-triazino[4,5-b]indazole-l(2H)thione gave 1,2,4-triazino-[4,5-b]indazoles. Nmr spectral data are reported. 相似文献
11.
The reaction of N-methylpryrrole-3,4-dicarboxaldehyde ) I )and N-methylpyrrole-2,3-dicarboxaldehyde ) 2 ) with sulfones affored thiepimo[4,5-c]-pyrrole 6,6-dioxides and the thiepimo[4,5-b]pyrrole 6,6-dioxides, respectively. Attempts to condense sulfides with 1 yielded the thiepino[4,5-c]-pyrrole ring system, however sulfides with 2 resulted in benzo-annelation. 相似文献
12.
Gazieva G. A. Lozhkin P. V. Baranov V. V. Kravchenko A. N. Makhova N. N. 《Russian Chemical Bulletin》2010,59(3):642-646
α-Ureidoalkylation of N-(2-acetylammoethyl)ureas with various 4,5-dihydroxyimidazoli-din-2-ones was systematically studied. Novel N-(2-acetylaminoethyl)glycolurils were obtained. Their yields were found to decrease both when moving from l,3-H2-to l,3-Alk2-4,5-dihydroxy-imidazolidin-2-ones and when increasing the size of the substituent at the second N atom in the starting acetylaminoethylurea.
The higher yields were achieved with 4,5-diphenyl-4,5-dihydroxyimidazolidin-2-one as the starting compound. 2-(2-Acetylaminoethyl)-4-methylgly-coluril
exhibits nootropic activity. 相似文献
13.
Giulia Menozzi Alberto Bargagna Luisa Mosti Pietro Schenone 《Journal of heterocyclic chemistry》1986,23(2):455-458
The 1,4-cycloaddition of sulfene to N,N-disubstituted (E)-4-aminomethylene-3,4-dihydro[1]benzothiepin-5(2H)-ones I occurred only in the case of aliphatic N,N-disubstitution to give in good yield 4-dialkylamino-3,4,5,6-tetrahydro[1]benzothiepino[4,5-e][1,2]oxathiin 2,2-dioxides, which are derivatives of the new heterocyclic system [1]benzothiepino[4,5-e][1,2]oxathiin. Also the reaction of I with chlorosulfene occurred only in the case of aliphatic N,N-disubstitution to afford chiefly trans-4-dialkylamino-3-chloro-3,4,5,6-tetrahydro-[1]benzothiepino[4,5-e][1,2]oxathiin 2,2-dioxides III in satisfactory yield. Adducts III were dehydrochlorinated with DBN to 4-dialkylamino-5,6-dihydro[1]benzothiepino[4,5-e][1,2]oxathiin 2,2-dioxides in good yield. 相似文献
14.
When 3-chloro-4,5-diaminopyridazine ( 2 ) was treated with sodium methylmercaptide in refluxing N,N-dimethylformamide, two heterocycles were formed and isolated, neither of which was the expected 3-methylthio-4,5-diaminopyridazine ( 3 ). A thorough spectral analysis of these heterocycles showed them to be 4-methylthioimidazo[4,5-d]pyridazine ( 5 ) and imidazo[4,5-d]pyridazine-4-thione ( 6 ). N,N-Dimethylformamide was found to provide the one carbon unit required for the formation of 5. The origin of 6 was shown to be a result of S-demethylation of 5. S-Demethylation of 3 could also be effected with sodium methylmercaptide in methyl sulfoxide without the occurrence of annulation. In methyl sulfoxide the process of demethylation was accelerated and occurred at lower temperature. 相似文献
15.
Reaction of 2′,6-dimethyl-2-nitrobiphenyl with triethyl phosphite gave 4,5-dimethyl-9-ethylcarbazole besides 4,5-dimethylcarbazole. In this reaction, 4,5-dimethylcarbazole was ethylated by triethyl N-(2′,6-dimethybiphenyl-2-yl)phosphorimidate and diethyl N-(2′,6-dimethylbiphenyl-2-yl)phosphoramidate, which arose from a nitrene-intermediate and triethyl phosphite. Analogous ethylations of carbazole with other phosphorimidate and phosphoramidates were investigated. 相似文献
16.
By the reaction of weak bases with N(2)-disubstituted 2-amino-4-thiazoliniminium chlorides 3, easily available by the reaction of thioureas 1 with α-chloroacetonitrile 2, N(2),N(2′)-persubstituted 2,4-diamino-5-(2-amino-4-thiazolyl)thiazoles 8 are formed. These new bis-thiazoles react, as exemplified with the dimorpholino derivative 8a, with different electrophilic reagent, such as phenyl isothiocyanate 9, 4-nitro-phenyldiazonium salt 11, or 4-dialkylaminobenzaldehydes 13 at their 5H-substituted thiazole moieties to give the corresponding thioanilides 10, azo compounds 12, and methine dyes 14, respectively. With sodium nitrite and the Vilsmeier reagent the thiazole 8a is transformed, via unstable intermediates, into the tricyclic 2,7-dimorpholinothiazolo[4,5-c]thiazolo[4,5-e]pyridazine 16 and 2,7-dimorpholinothiazolo[4,5-b]thiazolo[4,5-d]pyridine 19, respectively. 相似文献
17.
An efficient proline‐catalyzed synthesis of 4,5‐disubstituted‐N‐sulfonyl‐1,2,3‐triazoles has been accomplished from 1,3‐dicarbonyl compounds and sulfonyl azides. The developed reaction is suitable for various symmetrical and unsymmetrical 1,3‐dicarbonyl compounds, tolerates various functional groups and affords 4,5‐disubstituted‐N‐sulfonyl‐1,2,3‐triazoles in good yield with excellent regioselectivity. Rhodium‐catalyzed denitrogenative functionalization of 4,5‐disubstituted‐N‐sulfonyl‐1,2,3‐triazoles further demonstrates their utility in organic synthesis. 相似文献
18.
G. A. Gazieva P. V. Lozhkin V. V. Baranov Yu. V. Nelyubina A. N. Kravchenko N. N. Makhova 《Russian Chemical Bulletin》2009,58(12):2488-2493
α-Ureidoalkylation of N-[2-(dimethylamino)ethyl]urea with 1,3-unsubstituted, 1,3-dialkyl-, and 1,3-dimethyl-4,5-diphenyl-4,5-dihydroxyimidazolidin-2-ones(thiones)
was systematically studied. Hitherto unknown N-[2-(dimethylamino)ethyl]glycolurils and their hydrochlorides were synthesized. The yields of the target glycoluril hydrochlorides
decreased on going from 1,3-H2- to 1,3-dialkyl-4,5-dihydroxyimidazolidin-2-ones and increased with the introduction of phenyl groups at the positions 4
and 5 of the starting 4,5-dihydroxyimidazolidin-2-one. X-ray diffraction study showed that 2-[2-(dimethylamino)ethyl]glycoluril
crystallizes in the form of a conglomerate. 相似文献
19.
Xiao-Bo Ma Jing-Lin Zhang 《Phosphorus, sulfur, and silicon and the related elements》2013,188(1-4):227-231
Abstract The condensation of N-phenyl-N′-(2-hydroxylphenyl)urea or N-phenyl-N′-(2-aminophenyl)urea with tris(dia1kylamino)phosphine afforded derivatives of 4,5-benzo-1,3,2-oxaza (or diaza)-phospholane which formed intramolecular hydrogen bond. The cleavage of the amide bond to give N,N-dialky1-N′-phenylurea together with polymers of 1,3,2-benzodiazaphosphole was observed in the latter reaction. 相似文献
20.
A systematic investigation of α-ureidoalkylation of N-hydroxyalkylureas with 4,5-dihydroxy-1,3-dimethyl-4,5-diphenylimidazolidin-2-one allowed the discovery of a synthetic route
to earlier unknown N-hydroxyalkyl-1,5-diphenylglycolurils. The yields of these compounds decrease with lengthening and branching of the alkyl
chain in the starting ureas. 相似文献