A method has been developed for the synthesis of a new 18-membered nitrogen macroheterocycle via acid-catalyzed cyclocondensation of 1-[(2E,Z)-2-hydrazinylidene-2-phenylethyl]-5-methyl-1H-pyrazole-3-carbohydrazide which was obtained by hydrazinolysis of methyl 5-methyl-1-(2-oxo-2-phenylethyl)-1H-pyrazole-3-carboxylate.
Ethyl 3-phenyl-1H-pyrazole-5-carboxylate reacted with oxiranes to give mixtures of 2-phenyl-6-R-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-4-ones and ethyl 1-(2-hydroxy-3-R-propyl)-5-phenyl-1H-pyrazole-3-carboxylates. A probable mechanism for the formation of fused oxazine ring has been proposed.
A synthetic route has been proposed to 3-phenyl-1H-[1,4]oxazino[4,3-a]benzimidazol-1-one, which is the first representative of a new heterocyclic system. The transformation of the title compound to 4-phenyl-2,5-dihydro-1H-[1,2,5]triazepino[5,4-a]benzimidazol-1-one via reaction with hydrazine hydrate has been studied.
A modified procedure has been proposed for the synthesis of 2,7-diphenyl-5,8-dihydro-4 H -pyrazolo[5,1- d ][1,2,5]triazepin-4-one, and the possibility of transformation of the latter to the pyrazolo[1,5- a ]pyrazine system has been demonstrated. Functionalization of 2,7-diphenyl-5,8-dihydro-4 H -pyrazolo[5,1- d ][1,2,5]triazepin-4-one at the 4-position and fusion of a tetrazole or triazole ring at the C 4 –N 5 bond have been performed.
A synthetic approach to β-carbolines has been proposed on the basis of heterocyclization of ethyl 2-(2-benzoyl-1 H -indol-3-yl)acetate with N -methylformamide or ammonium acetate. Hydrazine hydrate proved to be inefficient in this reaction. The heterocyclization of dimethyl 2,2′-(2-benzoyl-1 H -indole-1,3-diyl)diacetate with ammonium acetate selectively afforded 2-(3-hydroxy-1-phenyl-9 H -pyrido[3,4- b ]indol-9-yl)acetamide. Treatment of dimethyl 2,2′-(2-benzoyl-1 H -indole-1,3-diyl)diacetate with hydrazine hydrate, followed by acid-catalyzed heterocyclization, gave methyl 2-(4-oxo-1-phenyl-4,5-dihydro-3 H -[1,2,5]triazepino[5,4- a ]indol-11-yl)acetate or 2-{4-oxo-1-phenyl-4,5-dihydro[1,2]diazepino[4,5- b ]indol-10(3 H )-yl}acetohydrazide, depending on the conditions.
Предложен метод синтеза неизвестных ранее пирроло- и индоло-1,4-эпокси[1,4]оксазепинов на основе реакции эпоксиметилирования 2-бензоилпиррола и 2-бензоилиндола. Изучены пути возможных трансформаций продуктов эпоксиметилирования.
A new procedure has been proposed for the synthesis of previously unknown pyrrolo- and indolo-1,4-epoxy[1,4]oxazepines by epoxymethylation of 2-benzoyl-1H-pyrrole and 2-benzoyl-1H-indoles with epichlorohydrin. Some transformations of the epoxymethylation products have been studied.
Предложен метод синтеза новой гетероциклической системы 7-метил-1-фенил-5,7-дигидро[1,2]диазепино[5,4-b]карбазол-4(3H)-она и новый подход к синтезу 1-R-6-метил-6H-пиридо[4,3-b]карбазол-3олов - близких аналогов природного алкалоида эллиптицина.
7-Methyl-1-phenyl-5,7-dihydro[1,2]diazepino[5,4-b]carbazol-4(3H)-one representing a new heterocyclic system has been synthesized starting from 2-(9-methyl-9H-carbazol-2-yl)acetic acid, and a new approach has been proposed to the synthesis of 1-R-6-methyl-6H-pyrido[4,3-b]carbazol-3-ols that are close analogs of the natural alkaloid ellipticine.
3,4-Dihydropyrimidines obtained by the Biginelli reaction react with hydrazine to give a mixture of N-[(3,5-dimethyl-1H-pyrazol-4-yl)(R)methyl]ureas and 4-R-3,7a-dimethyl-1,3a,4,5,7,7a-hexahydro-6H-pyrazolo[3,4-d]pyrimidin-6-ones. The latter transform into N-[(3,5-dimethyl-1H-pyrazol-4-yl)(R)methyl]ureas in an acidic medium.
An approach is developed to the synthesis of 2-methyl-7-phenyl-5,8-dihydro-4H-pyrazolo[5,1-d]-[1,2,5]triazepin-4-one, based on the recyclization of 2-methyl-6-phenyl-4H-pyrazolo[5,1-c][1,4]oxazin-4-one with hydrazine.
A method of synthesis is proposed and alternative mechanisms of formation of 1,3,6-trimethyl-6Hpyrano[ 4,3-b]carbazole-2-pyrylium perchlorate and its recyclization to 1,3,6-trimethyl-6H-pyrido[4,3-b]- carbazole, a close analog of the natural alkaloid ellipticine, are discussed.
Strategies of synthesis of pyrrolo[3,4-c]pyridines were developed based on cyclization of 3-phenacyl-4-ethoxycarbonyl(acetyl)pyrrole derivatives reacting with N-methylformamide or formamide, and also on recyclization of pyrrolo[3,4-c]pyrylium salts under the action of ammonium acetate and hydrazine acetate. The influence of substituents in initial reagents on composition of reaction products was studied.
A preparative procedure has been developed for the synthesis of substituted 5,7-dihydropyrrolo-[3,4-d][1,2]diazepines by recyclization of 6-phenylpyrano[3,4-c]pyrrol-4(2H)-one with hydrazine hydrate. The stability of the seven-membered ring in the products under acidic conditions, alkylation, and heteroring fusion to the diazepine ring have been studied.
A method has been developed for the cyclization of 4-aryl-1-hydrazino-5H-2,3-benzodiazepine and 1-aryl-4-hydrazino-5H-2,3-benzodiazepine into 3-R-6-aryl-7H-[1,2,4]triazolo[3,4-a]- and 3-R-6-aryl-7H-[1,2,4]triazolo[4,3-c]benzodiazepine derivatives with various substituents in the triazole ring.
ChemInformVolume 44, Issue 46 Heterocyclic Compounds ChemInform Abstract: 4-Aryl-1-hydrazino-5H-2,3-benzodiazepine (III) and 1-Aryl-4-hydrazino-5H-2,3-benzodiazepine (XI) in the Synthesis of Condensed [1,2]Diazepines. O. I. Kharaneko, O. I. Kharaneko Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this authorV. Yu. Popov, V. Yu. Popov Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this authorS. L. Bogza, S. L. Bogza Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this author O. I. Kharaneko, O. I. Kharaneko Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this authorV. Yu. Popov, V. Yu. Popov Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this authorS. L. Bogza, S. L. Bogza Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this author First published: 24 October 2013 https://doi.org/10.1002/chin.201346173Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume44, Issue46November 12, 2013 RelatedInformation
ChemInformVolume 44, Issue 34 Heterocyclic Compounds ChemInform Abstract: Novel Strategy for the Synthesis of the Pyrrolo[3,4-d][1,2]diazepine Heterocyclic System. O. I. Kharaneko, O. I. Kharaneko Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this authorS. L. Bogza, S. L. Bogza Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this author O. I. Kharaneko, O. I. Kharaneko Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this authorS. L. Bogza, S. L. Bogza Litvinenko Inst. Phys. Org. Coal Chem., Natl. Acad. Sci. Ukr., Donetsk 83114, UkraineSearch for more papers by this author First published: 01 August 2013 https://doi.org/10.1002/chin.201334174Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume44, Issue34August 20, 2013 RelatedInformation
A series of S-substituted and 1,2-annelated derivatives of 2,3-benzodiazepine has been obtained on the basis of 2,3-benzodiazepine-1-thione.
