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1.
The conversion of 2-acylamino-3-amino-1,4-naphthoquinones (II) to the corresponding 2-substituted 1H-naphth[2,3-d]imidazole-4,9-diones (I) under both alkaline and acid catalyzed conditions has been effected and the results compared. Treatment of 3-(4′-chlorobutanonyl-amino)-3-amino-1,4-naphthoquinone (He) with aqueous ethanolic sodium hydroxide solution gives 1,2-butanonaphth[2,3-d]imidazole-4,9-dione (V); whereas, treatment of lie with refluxing formic acid gave 2-(4′-chlorobutyl)-1H-naphth[2,3-d]imidazole-4,9-dione. Treatment of 2-substi-tuted 1H-naphth[2,3-d]imidazole-4,5-diones in DMF with alkyl halides in the presence of potassium carbonate affords the expected 1,2-disubstituted naphth[2,3-d]imidazole-4,9-diones (VI). The spectral properties of I, II, V and VI as well as those of some 2-acylamino-3-chloro-1,4-naphthoquinones IV are discussed. 相似文献
2.
P. S. Silaichev N. V. Kudrevatykh A. N. Maslivets 《Russian Journal of Organic Chemistry》2012,48(8):1103-1106
1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones react with alkyl vinyl ethers and 3,4-dihydro-2H-pyran affording 1,4-diaryl-7a-aroyl-6-ethoxy-7,7a-dihydropyrano[4,3-b]pyrrole-2,3(1H,6H)-diones and 1,4-diaryl-9baroyl-1,7,8,9,9a-hexahydro-5aH-pyrano[3??,2??:5,6]pyrano[4,3-b]-pyrrole-2,3-diones respectively. 相似文献
3.
Au?ra Voskien? Birut? Sapijanskait? Vytautas Mickevi?ius Kristina Kantminien? Maryna Stasevych Olena Komarovska-Porokhnyavets Rostyslav Musyanovych Volodymyr Novikov 《Monatshefte für Chemie / Chemical Monthly》2011,17(1):529-537
Abstract
Mono- and disubstituted [(tetrahydro-2,4-dioxopyrimidin-1(2H)-yl)phenoxy]naphthalene-1,4-diones were synthesized by the reaction of dihydro-1-(3-hydroxy- and 4-hydroxyphenyl)pyrimidine-2,4(1H,3H)-diones and their 5- and 6-methyl derivatives with 2,3-dichloro-1,4-naphthoquinone. Their stability in alkaline and acidic media was investigated. Four of the compounds exhibited good antimicrobial activity against Staphylococcus aureus, Mycobacterium luteum, Candida tenuis, and Aspergillus niger. 相似文献4.
Vostrov E. S. Leont'eva E. V. Tarasova O. P. Maslivets A. N. 《Russian Journal of Organic Chemistry》2003,39(1):103-107
Aroyl(phenyl)ketenes generated by thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones undergo [4+2]-cyclodimerization to 3-aroyl-6-aryl-3,5-diphenyl-3,4-dihydro-2H-pyran-2,4-diones. Heating of the latter leads to rearrangement with formation of 4-aroyloxy-6-aryl-3,5-diphenyl-2H-pyran-2-ones. Thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones in the presence of carbonyl compounds yields 6-aryl-5-phenyl-4H-1,3-dioxin-4-ones. 相似文献
5.
P. S. Silaichev N. V. Kudrevatykh Z. G. Aliev A. N. Maslivets 《Russian Journal of Organic Chemistry》2012,48(2):253-256
1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones react with styrene to form substituted 7,7a-dihydropyrano[4,3-b] pyrrole-2,3(1H,6H)-diones whose structure was confirmed by XRD analysis. The crystal and molecular structure of 7a-(2,5-dimethylbenzoyl)-4-(2,5-dimethyl-phenyl)-1-(4-methoxyphenyl)-6-phenyl-7,7a-dihydropyrano[4,3-b] pyrrole-2,3(1H,6H)dione was examined. 相似文献
6.
V. V. Khalturina Yu. V. Shklyaev Z. G. Aliev A. N. Maslivets 《Russian Journal of Organic Chemistry》2009,45(5):728-734
5-Arylfuran-2,3-diones and (Z)-alkyl 4-aryl-2-hydroxy-4-oxobut-2-enoates react with 3,3-dialkyl-1-methyl-3,4-dihydroisoquinolines to give (2Z,5Z)-1-aryl-3-hydroxy-5-[3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene]pent-2-ene-1,4-diones whose structure has been proved by XRD analysis. 相似文献
7.
An unprecedented route for the synthesis of N-1 substituted 5-(phenylsulfanyl)-1,4-dihydropyrazine-2,3-diones is disclosed starting from 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones. The method comprises treatment of various 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones with Na2CO3 in water under microwave irradiation providing the respective 5-(phenylsulfanyl)-1,4-dihydropyrazine-2,3-diones in good yields, via hydrolysis of the thioether bond and subsequent nucleophilic displacement of the chlorine by the in situ generated thiophenol. The obtained compounds are excellent precursors for the diversity oriented synthesis of pharmacologically active α,β-dicarbonyl compounds. 相似文献
8.
O. A. Sof''ina N. M. Igidov E. N. Koz''minykh N. N. Trapeznikova Yu. S. Kasatkina V. O. Koz''minykh 《Russian Journal of Organic Chemistry》2001,37(7):1017-1025
Acylpyruvic acids readily react with 2,3-diaminopyridine to form (Z)-3-acylmethylene-1H-3,4-di- hydropyrido[2,3-b]pyrazin-2-ones. 5-Aryl-2,3-dihydrofuran-2,3-diones which can be regarded as lactones derived from -enolized aroylpyruvic acids react with 2,3-diaminopyridine under mild conditions, yielding regioisomeric (Z)-2-aroylmethylene-4H-1,2-dihydropyrido[2,3-b]pyrazin-3-ones. The structure of the products and reaction chemoselectivity are discussed. 相似文献
9.
E. N. Kozminykh N. M. Igidov G. A. Shavkunova V. O. Kozminykh 《Russian Chemical Bulletin》1997,46(7):1285-1290
2-p-Chlorobenzoylmethylene-5-phenyl-2,3-dihydro-3-furanone reacts with arylamines orN-arylideneamines to form the products of ring opening, 1,6-diaryl-1-arylamino-4-hydroxy-1,4-hexadiene-3,6-diones. The reaction
of 5-aryl-2-p-chlorobenzoylmethylene-2,3-dihydro-3-furanones witho-aminophenol afforded 3-p-chlorobenzoylmethylene-3,4-dihydro-2H-benzo[b]-1,4-oxazin-2-one. Nucleophilic attack of amines is directed either to electrophilic centers at the C(5) and C(2) atoms or
to the carbonyl group of the 2-phenacylidene substituent of the 3-oxofuran ring.
For communication 15, see Ref. 1.
Translated fromIzestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1340–1345, July, 1997. 相似文献
10.
《合成通讯》2012,42(1):129-135
AbstractAn expeditious, one-pot multicomponent reaction has been developed for the synthesis of (E)-2-(benzylideneamino)-5-mercapto-4H-1,2,4-triazol-3-yl)-2,3-dihydrophthalazine-1,4-dione derivatives. Condensation of 4-amino-5-hydrazino-4H-1,2,4-triazole-3-thiol with phthalic anhydride and aromatic aldehyde afforded the (E)-2-(benzylideneamino)-5-mercapto-4H-1,2,4-triazol-3-yl)-2,3-dihydrophthalazine-1,4-diones in acetic acid medium with excellent yields. All the synthesized compounds were characterized by their analytical and spectral data. 相似文献
11.
Kazuhiro Kobayashi Hideo Tanaka Koujirou Tanaka Keiichi Yoneda Osamu Morikawa Hisatoshi Konishi 《合成通讯》2013,43(23):4277-4291
The reaction of 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione with various alkenes or terminal alkynes in the presence of cerium(IV) ammonium nitrate (CAN) afforded the corresponding 5,6-dihydrofuro[2,3-d]pyrimidine-2,4(1H,3H)-diones or furo[2,3-d]pyrimidine-2,4(1H,3H)-diones in moderate to good yields. 相似文献
12.
E. S. Vostrov E. V. Leont'eva O. P. Tarasova A. N. Maslivets 《Russian Journal of Organic Chemistry》2004,40(7):1058-1061
Thermal decarbonylation of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones gives rise to intermediate aroyl(phenyl)ketenes which react with nonactivated Schiff bases, N,N'-dicyclohexylcarbodiimide, and p-di-methylaminobenzonitrile according to the [4 + 2]-cycloaddition pattern with formation of 6-aryl-5-phenyl-4H-1,3-oxazin-4-ones. Reactions of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones with activated Schiff bases at a temperature below the thermolysis temperature lead to 4-aroyl-4-phenyltetrahydropyrrole-2,3-diones. 相似文献
13.
L. M. Gornostaev M. V. Vigant O. I. Kargina A. S. Kuznetsova Yu. G. Khalyavina T. I. Lavrikova 《Russian Journal of Organic Chemistry》2013,49(9):1354-1357
2-Aryl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-diones were synthesized by treatment of 2-benzylamino-1,4-naphthoquinones with a mixture of nitric and sulfuric acids in acetic acid. 相似文献
14.
Noboru Matsumura Osamu Mori Toshio Takeguchi Yasuyuki Okumura Kazuhiko Mizuno 《Journal of heterocyclic chemistry》2004,41(6):873-876
Photoirradiation of acetone solutions of 2,3‐diallyl‐6,7‐dihydro‐5H‐2a‐thia(2a‐SIV)‐2,3,4a, 7a‐tetraazacyclopent[cd]indene‐ 1,4(2H,3H)‐dithione ( 1 ) in the presence of excess thioacetic acid and thiobenzoic acid afforded addition products, 2,3‐bis(3‐acetylthiopropyl)‐ and 2,3‐bis(3‐benzoylthiopropyl)‐6,7‐dihydro‐5H‐2a‐thia(2a‐SIV)2,3,4a, 7a‐tetraazacyclopent[cd]indene‐1,4(2H,3H)‐dithiones, respectively, in good yields. These photoaddition reactions were facilitated by the addition of oxygen. 相似文献
15.
P. S. Silaichev N. V. Kudrevatykh Z. G. Aliev A. N. Maslivets 《Russian Journal of Organic Chemistry》2010,46(10):1546-1549
1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones reacted with benzyl- and phenylhydrazines to give N-aryl-2-(5-aryl-3-aroyl-1-benzyl(phenyl)-1H-pyrazol-4-yl)-2-oxoacetamides whose structure was proved by X-ray analysis. 相似文献
16.
Kazuhiro Kobayashi Hiroyasu Takeuchi Shinzo Seko Yoshikazu Kanno Sachiko Kujime Hiroshi Suginome 《Helvetica chimica acta》1993,76(8):2942-2950
The 2,3-dihydro-1H-benz[f]indole-4,9-diones 3a–d , h were formed in a one-step reaction in 13–82% yield by an unprecedented [3 + 2] regioselective photoaddition of 2-amino-1,4-naphthoquinone ( 1 ) with various electronrich alkenes 2 (Scheme 1, Table). The [3 + 2] photoadducts derived from 1 with vinyl ethers and vinyl acetate gave 1H-benz[f]indole-4,9-diones 4e , f , i , in 33–72% yield, by spontaneous loss of the corresponding alcohol or AcOH from the resulting adducts; 4i has a kinamycin skeleton. The [3 + 2] photoaddition also took place on irradiation of the differently substituted amino-1,4-benzoquinones 6 , 7 , and 12 and excess alkenes 2 in benzene, giving 1H-indole-4,7-dione derivatives 13 and 14 (Scheme 3), 15a and 16 (Scheme 4), and 18 (Scheme 4), respectively. The initial products in these photoadditions were proved to be hydroquinones, the air oxidation of which yielded the heterocyclic quinones; 2,3-dihydro-2-methoxy-2-methyl-5-phenyl-1H-indole-1,4,7-triyl triacetate ( 19 ) was isolated after treatment of the crude photoaddition mixture obtained from 2-amino-5-phenyl-1,4-benzoquinone ( 7 ) and 2-methoxyprop-1-ene ( 2f ) with Ac2O and pyridine under N2. A pathway leading to the annelated hydroquinones involving ionic intermediates arising from an electron transfer in these photoadditions is proposed (Scheme 5). 相似文献
17.
A number of 5-amino-2,3-dihydro-lH-1,4-benzodiazepines (II) have been prepared from the reaction of 5-methylmercapto-2,3-dihydro-1H-1,4-benzodiazepine (I) with amines. Another alternate approach based on the cyclodehydration of the ureic compounds (IV) was unsuccessful. The synthesis of I was accomplished by methylation of the 1,2,3,4-tetrahydro-5H-5-thioxo-1,4-benzodiazepine (VI) with dimethyl sulfate in methanol-dioxane. Another attempted method for the synthesis of I is also presented. J. Heterocyclic Chem., 14, 985 (1977) 相似文献
18.
V. V. Khalturina Yu. V. Shklyaev Z. G. Aliev A. N. Maslivets 《Russian Journal of Organic Chemistry》2010,46(4):539-542
5-Arylfuran-2,3-diones react with (Z)-2-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene]acetamides to give (3E,5Z)-5-(2-aryl-2-oxoethylidene)-3-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene]-pyrrolidine-2,4-diones. The crystalline and molecular structures of one of the products were determined by X-ray
analysis. 相似文献
19.
N. G. Vinokurova K. F. Turchin B. P. Baskunov M. U. Arinbasarov 《Russian Journal of Organic Chemistry》2002,38(6):868-871
Reactions of roquefortin with alkyl chloroformates provide 3-(1-(alkoxycarbonyl)imidazol-4-ylmethylene]-10b-(1,1-dimethyl-2-propenyl)-5a,10b,11,11a-tetrahydro-2H-pyrazinol[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,6H)-diones. 相似文献
20.
Reactions of 6-Amino-5-Cyano-3-Methyl-1,4-Diphenyl-1H 4H-Pyrano[2,3-C]Pyrazole and its Methanimidate
Reaction of 6-amino-5-cyano-3-methyl-1,4-diphenyl- 1H,4H-pyrano[2,3-c]pyrazole 1 with triethyl orthoformate in acetic anhydride gave its methanimidate 2, which reacts with primary aliphatic and aromatic amines to give 4,6-dihydro-3-methyl-1,4-diphenyl-6- (alkyl)pyrazolo[4′,3′:5,6]pyrano[2,3-d]pyrimidine-5(lH)- imine 3 and the starting compound 1 , respectively. Treatment of 1 with o-aminophenol gave 5-(2-benzoxalyl)- 1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazol- 6-amine 9. 相似文献