Reactions of 4-oxo-1,3-benzoxazinium perchlorates with guanidines

Condensation of 2-methyl-4-oxo-1,3-benzoxazinium perchlorate with various aromatic and heterocyclic aldehydes provided previously unknown arylvinyl-and hetarylvinyl-substituted salts whose recyclization under treatment with guanidine resulted in formerly undescribed 1,3,5-triazines. The reaction of perchlorates obtained with guanidinebenzoxazole led to the formation of bishetarylamines, with guanidinebenzimidazole formed triazinebenzimidazoles, the cyanoguanidine reacted with 4-oxo-1,3-benzoxazinium perchlorates to give cyanamides.     

Reactions of 4-oxo-1,3-benzoxazinium perchlorates with sodium borohydride

Reduction of 4-oxo-1,3-benzoxazinium perchlorates with sodium borohydride depending on the structure of starting salt and the reaction conditions leads to different products. 2-Alkyl- and 2-phenylsubstituted salts react with sodium borohydride to give 2,3-dihydro-4-oxo-1,3-benzoxazines. 2-Arylvinyl- and 2-heterylvinyl-substituted perchlorates either form 4-oxo-1,3-benzoxazines or undergo hydrogenation to arylor heterylethyldihydrobenzoxazinones.     

Synthesis of 4-alkylthio-2-(o-hydroxyphenyl)-1,3,5-triazines by recyclization of 4-oxo-1,3-benzoxazine perchlorates

A method has been developed for synthesis of 4-alkylthio-2-(o-hydroxyphenyl)-1,3,5-triazines by treatment of 4-oxo-1,3-benzoxazine perchlorates with S-methyl, benzyl, and allyl-isothioureas.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1658–1661, December, 1989.     

synthesis and some transformations of 4-oxo-2-(β-ethoxyvinyl)-4H-1,3-benzoxazinium salts

A method was developed for the synthesis of 4-oxo-(-ethoxyvinyl)-4H-1,3-benzoxazinium salts by condensation of oxo-2-alkylbenzoxazinium salts by condensation of oxo-2-alkylbenzoxazinium salts with ethyl orthoformate. During hydrolysis and aminolysis, attack of the nucleophile is directed to the -carbon atom of the benzoxazinium salts. The previously unknown 2-formylmethylene-4-oxo-3,4-dihydro-2H-1,3-benzoxazines and their nitrogen derivatives were obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 322–327, March, 1977.     

Recyclization of 4-oxo-1,3-benzothiazinium salts. Synthesis of o-mercaptophenyl-1,2,4-triazoles and metal chelates based on them

A method based on the reaction of 4-oxo-1,3-benzothiazinium perchlorates with hydrazines is developed for synthesizing 5-(o-mercaptophenyl)-1,2,4-triazoles. Their complexes with Ni(II), Co(II), and Zn(II) are prepared. The o-mercaptophenyltriazoles are capable of undergoing oxidative dimerization to give disulfides.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1220–1226, September, 1991.     

Condensation of 2-alkyl-4-oxo-1,3-benzoxazinium salts with carbonyl compounds and their heteroanalogs

A method is proposed for the synthesis of 2-(-dimethylaminovinyl)-4-oxo-1,3-benzoxazinium salts and dimethyl (4-oxo-3H-1,3-benzoxazine-2-methylene) sulfonium salts by condensation of 2-alkylbenzoxazinonium salts with dimethylformamide and dimethyl sulfoxide.Translated from Khimiya Geterotsiklichesikikh Soedinenii, No. 3, pp. 328–331, March, 1977.     

Unusual Recyclization of 2(1-Bromostyryl)-4-oxo-1'3-benzoxazinium Perchlorate into 2'3'4'5-Tetrahydro-1'4-benzoxazepine-4'5-dione

Russian Journal of Organic Chemistry -     

Recyclization reactions of heterocyles. XVII. Hydrazination of 1, 3, 4-oxadiazolium salts

2, 5-Diaryl-3-alkyl-1, 3, 4-oxadiazolium salts react with hydrazine to give acyclic hydrazinolysis products or products of recyclization with participation of the carbon atom in the 2 position of the oxadiazole ring, i.e., dihydro-sym-tetrazines and N-amino-sym-triazoles (with hydrazine) and 2-phenyl-5-aryl-1, 3, 4-oxadiazoles (with benzoylhydrazine) or formazans (with phenylhydrazine).See [1] for communication XVI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 629–634, May, 1976.     

Synthesis of 1-(benzothiazol-2-yl)-5-(o-hydroxyphenyl)-1H-1,2,4-triazoles

Recyclization of 4-oxo-1,3-benzoxazinium perchlorates by the action of benzothiazolylhydrazine gave previously unknown benzothiazolyl-substituted 1,2,4-triazoles that attract interest as potential biologically active substances. The structure of the isolated compounds was determined on the basis of their IR and ¹H and ¹³C NMR spectra.     

Molecular and crystal structure of 1-phenyl-3-methyl-5-(o-hydroxyphenyl)-1,2,4-triazole

A choice between the possible mechanisms of the recyclization of 4-oxo-1,3-benzoxazine salts due to reaction with phenylhydrazine was made based on the x-ray structure of 1-phenyl-3-methyl-5-(o-hydroxyphenyl)-1,2,4-triazole.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 109–111, January, 1989.     

3-(4-吡啶基)-4-(6-取代色酮-3-基-亚甲氨基)-5-芳氨基-1,2,4-三唑的合成

N-芳基-N'-[(4-吡啶基)羰基]氨基硫脲用85%的水合肼环化, 得到3-(4-吡啶基)-4-氨基-5-芳氨基-1,2,4-三唑(2a～2c). 然后再与3-甲酰基色酮(3a～3d)反应, 制备得到了一系列新化合物: 3-(4-吡啶基)-4-(6-取代色酮-3-基亚甲氨基)-5-芳氨基-1,2,4-三唑(4a～4c, 5a～5c, 6a～6c, 7a～7c). 化合物的结构经元素分析, IR, ¹H NMR和MS确证.     

Recyclization of 2-(2-acylethyl)pyridinium salts

Recyclization of 2-(2-acylethyl)pyridinium salts on treatment with nucleophiles may occur in different ways, to give heterocyclic compounds of various classes, namely indoles (the Kost-Sagitullin reaction products), 4-aminoindoles, and 3-hydroxy-1,2,3,4-tetrahydroquinolines, the formation of which constitute novel reactions in the recyclization of pyridinium salts.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1217–1225, September, 1990.     

Recyclization of 3-alkyl- and 1,3-dialkylisoquinolinium salts to naphthylamines

3-Methyl- and 3-benzylisoquinolinium salts undergo rearrangement to 2-alkylaminonaphthalenes under the influence of alcohol solutions of alkylamines. The rearrangement of 1,3-dimethyl- and l-methyl-3-benzylisoquinolinium salts leads to both 1- and 2-alkylaminonaphthalenes with predominance of the former.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1272–1277, September, 1980.