New organic nitrates. II. Synthesis of 2H-pyrido[2,3-e]-1,3-oxazine-2,4(3H)-diones, 2H-pyrido[4,3-e]-1,3-oxazine-2,4(3H)-diones, 2H-pyrido[4,3-e]-1,3-oxazin-4(3H)-ones, 2H-thieno[2,3-e]-1,3-oxazin-4(3H)-ones and 2H-thieno[3,4-e]-1,3-oxazin-2,4(3H)-diones

The preparation and the physico-chemical characterization of 2H-pyrido[2,3-e]-1,3-oxazine-2,4(3H)-diones, 2H-pyrido[4,3-e]-1,3-oxazine-2,4(3H)-diones, 2H-pyrido[4,3-e]-1,3-oxazin-4(3H)-ones, 2H-thieno[2,3-e]-1,3-oxazin-4(3H)-ones and 2H-thieno[3,4-e]-1,3-oxazine-2,4(3H)-diones are reported.     

Cyanine dyes from naphtho [1,2-6]thiazolo[3,2-d][1,4]thiazine

Deeply colored cyanine dyes have been synthesized from the previously unknown 3-methyl-12H-naphtho[1,2-b]thiazolo[3,2-d][1,4]thiazinium salts. It is assumed that the deep color of the new cyanines is connected with the conversion of the nonaromatic 1,4-thiazine ring in the dye molecule into an aromatic thiazine ring with three double bonds in a six-membered ring.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1282–1284, September, 1973.     

New synthesis of 6,7-dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones

Russian Journal of Organic Chemistry -     

Structure of reaction products of substituted [1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-ones with amines and hydrazines

Reactions of 2-(4-methylphenyl)[1,3]triazolo[3,2-b][1,2,4]thiazol-6(5H)-one and 5-benzylidene-2-(4-methylphenyl)[1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-one with amines and hydrazines of diverse structures were studied. The structure of the reaction products was established.     

L-proline-catalyzed 1,3-dipolar cycloaddition of some Schiff bases to methyl 4-[1-oxo-2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)ethyl]phenylcarbamate

Russian Journal of Organic Chemistry -     

Synthesis of 5H-5-oxobenzimidazo[2,1-b]pyrido[3,2-e][1,3]thiazine,A novel ring system

Reaction between 2-chloronicotinic acid chloride and 2-mercaptobenzimidazole afforded 5H-5-oxobenzimidazo[2,1-b]pyrido[3,2-e][1,3]thiazine, a novel heterocyclic ring system. The assigned structure was confirmed by means of mass spectrometry.     

Molecular structure of 10,10-dimethyl-7H-pyrano[4′,3′:4,5]thieno[3,2-e]-(1,2,4)-triazolo[2,3-e]pyrimidine

Institute of Fine Organic Chemistry, Armenian Academy of Sciences. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences. Translated fromZhurnal Strukturnoi Khimii, Vol. 35, No. 5, pp. 197–199, September–October, 1994.     

Synthesis of (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-5,10-diones

A convenient method was developed for the combinatorial synthesis of substituted (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]-diazepine-5,10-diones. The structure and the most probable conformation of (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-5,10-dione in solution was established by NMR spectroscopy and calculations using the Gaussian program.

     

Synthesis and combinatorial approach of the reactivity of 6- and 7-arylthieno[3,2-d][1,3]oxazine-2,4-diones

This paper describes a general procedure for the synthesis of new substituted thiaisatoic anhydrides or 6- or 7-aryl-1H-thiéno[3,2-d][1,3]oxazine-2,4-diones 3a-j and 4a-f. They were synthesized in large scale under microwave heating conditions with high yields. The reactivity vs nucleophilic reagents of these compounds was studied and permitted to develop a simple combinatorial procedure to synthesize a library of new thiophene ureidoacids 7a-j and 8a-j.     

Pyrroloindoles. 6. New synthesis of 1H, 5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole

Ethyl pyruvate 1-acetyl-5-indolinylhydrazone was obtained by diazotization of 1-acetyl-5-aminoindoline with subsequent reduction of the diazonium salt and condensation of the hydrazine with ethyl pyruvate. A mixture of hydrogenated derivatives of linear and angular pyrroloindoles is formed as a result of cyclization of the hydrazone in polyphosphoric acid esters. Subsequent hydrolysis, decarboxylation, and dehydrogenation lead to 1H,5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo-[3,2-e]indole.See [1] for Communication 5.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 504–507, April, 1982.     

A novel synthesis of substituted 3-amino and 3-thio pyrimido[5,4-e]-1,2,4-triazine-5,7(1H,6H)-diones

Fervenulin is a natural product that has been extensively studied due to its molecular features and breadth of biological activities. Published studies have reported the generation of numerous analogues of the bicyclic pyrimidotriazinodione core. One underrepresented subclass are compounds with electron releasing atoms bonded directly to the C-3 position. We report an efficient and straightforward synthesis of compounds with substituted amino and thio functionality attached to the C-3 position. These are derived from a common 3-chloro precursor that is made in six steps in 15.8% overall yield from a starting chlorouracil. Our methodology should be applicable to the synthesis of C-3 ether congeners also, and through previously described chemistry be expandable to incorporating diversity at the N-6 position of the pyrimidotriazinodione core. The chemistry reported herein expands possibilities for the generation of diverse libraries of substituted pyrimidotriazinediones for future studies.     

Synthesis and Antimicrobial Activity of 2-[5-(R-Benzyl)-4-oxo-1,3-thiazolidin-2-ylidene]-3-oxobutanenitrile and [2-(1-Cyano-2-oxopropylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetic Acid Derivatives

Russian Journal of Organic Chemistry - The reactions of 2-cyano-3-oxobutanethioamide with ethyl 3-aryl-2-bromopropanoates and dialkyl acetylenedicarboxylates afforded a combinatorial library of new...     

Synthèse et propriétés photochromiques de 1, 3-dihydrospiro[2H-indole-2,3′-[3H]pyrimido[5,4-f][1,4]benzoxazines] et de 1,3-dihydrospiro[2H-indole-2,7′-[7H]thiazolo[5,4-f][1,4]benzoxazines]

Synthesis and Photochrmic Characteristics of 1,3-Dihydrospiro[2H-indole-2,3′-[3H-]pyrimido[5,4-f][1,4]benzoxazines] and 1,3-Dihydrospiro[2H-indole-2,7′[7H]thiazolo[5,4-f][1,4]benzoxazines] Two new series of 1,3-dihydrospiro[2H-indole-ozazine] derivatives were synthesized, the 1,3-dihydrospiro[2H-indole-2,3′-[3H]pyrimido[5,4]pyrimido[5,4-f][1,4]benzoxaines] 4-10 and the 1,3-dihydrospiro[2H-indole2,7′-[7H]thiazolo-[5,4-f][1,4]benzoxaines] 11–17 . These series extend the available range of photochromic properties (rate constant of thermal bleaching, UV/VIS spectrum of the opened coloured form, and photocoloration yield), an interesting feature of variable-transmission materials. The synthesis of these compounds (Scheme 1) required the preliminary synthesis of intermediate β-hydroxy-α-nitrosotherocycles 18 and 19 (Scheme 2). Important amounts of a coloured, non-photochromic, stable secondary product (See 20 ) were found in the condensation in the spiro[indole-thiazolobenzoxazine] series. The photochromic characteristics of the new derivatives were determined using a flash-photolysis apparatus coupled to a fast-scanning spectrometer. The role of the heteroatoms in the oxazine moiety and the role of substitutents in the indole moiety were investigated quantitatively through the study of the photochromic properties and the solvent effects. The presence of an S-atom gives rise to interesting properties which open up new prospects for synthesis and application.     

Pyrrolo [1,2-a] [1,3,5] triazine-2,4(1H, 3H)-diones. III—Fragementation under electron-impact

The mass spectra of eight pyrrolo[1,2-a][1,3,5]triazie-2,4(1H, 3H)-diones have been examined. An unusual feature in the fragmentation of those compounds having a 7-alkoxycarbonyl function, namely loss of the whole ester grouping with concomitant hydrogen rearrangement, is discussed.