Synthesis of n-(phenoxathiin-2-carbonyl)-or N-(thianthrene-2-carbonyl)-N′-arylthioureas

The reactions of phenoxathiin-2-carbonyl-or thianthrene-2-carbonyl-isothiocyanates with certain primary amines lead to the formation of corresponding N-substituted-N-hetaroylthiocarbamides. The aforementioned isothiocyanates were obtained in situ by reactions of phenoxathiin-2-or thianthrene-2-carbonyl chlorides with KSCN. The new compounds were characterized by elemental analysis and spectral data (IR,¹H and¹³C NMR).Analytical Laboratory-Biofarm, 99 Logofat Tautu Street, Bucharest, Roumania. Faculty of Pharmacy, Organic Chemistry Departament, University of Medicine and Pharmacy Carol Davila, 6 Traian Vuia Street, Bucharest, Roumania, Faculty of Chemistry, Organic Chemistry Department, University of Bucharest, 90–92 Panduri Road, 76233, RoumaniaPublished in Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1681–1686, December, 1999.     

Phenoxathin chemistry. Remarks concerning the benzoylation reaction of phenoxathin

Benzoylation of phenoxathiin leads to a mixture of 2- and 3-benzoylphenoxathiins. Starting from 3-phenoxathiincarbonyl chloride and benzene in the presence of anhydrous aluminum chloride, 2-benzoylphenoxathiin was obtained instead of the 3-substituted isomer. Treating 3-benzoylphenoxathiin with aluminum chloride and hydrogen chloride a rearrangement reaction took place, leading to 2-benzoylphenoxathiin.Faculty of Chemistry, Organic Chemistry Department, University of Bucharest, 90–92 Panduri Road, Romania 76233. Romanian Academy, C. D. Nenitzescu Institute of Organic Chemistry, Splaiul Independentei, 202, Bucharest, Romania. Faculty of Pharmacy, Organic Chemistry Department, University of Medicine and Pharmacy Carol Davila, 6 Traian Vuia Street, Bucharest, Romania. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 999–1003, July, 1998.     

A convenient synthesis of pyrrolo[2,3-<Emphasis Type="Italic">b</Emphasis>]pyridines and pyrido[2′,3′:5,4]pyrrolo[2,3-<Emphasis Type="Italic">d</Emphasis>]pyrimidines

2-Chloro-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile was taken as versatile building block that allows the synthesis of 1H-pyrrolo[2,3-b]pyridine, thieno[2,3-b]pyridine and pyrido[2′,3′:5,4]pyrrolo[2,3-b]pyrimidine systems. Some of the synthesized compounds were screened as antibacterial agents. Correspondence: Shawkat A. Abdel-Mohsen, Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt.     

Orientation effects in phenoxathiin acetylation and formylation

In acetylation and formylation of phenoxathiin, besides 2-acyl-substituted main products, the 3-isomers form in ca. 10% yield. The structure of 3-acetylphenoxathiin isolated by fractional crystallization from the mixture resulted after acetylation was proved by means of physical and chemical methods.Faculty of Chemistry, Organic Chemistry Department, University of Bucharest, 90-92 Panduri Road, Romania. SINDAN S.R.L. 11 1 Mai Blv., Bucharest, Romania.Published in Khlmiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1261–1265, September, 1996. Original article submitted May 8, 1996; revision submitted July 30, 1996.     

Recyclization of 1,3-dimethylbenzo[b]furo[2,3-c]- and 1,3-dimethylbenzo[b]thieno[2,3-c]pyrylium when treated with secondary amines. Synthesis of 3-dialkylamino derivatives of dibenzofuran and dibenzothiophene

We have established that 2,4-dimethylbenzo[b]furo[3,2-c]pyrylium and 2,4-dimethylbenzo[b]thieno[3,2-c]pyrylium salts can undergo recyclization to 3-dialkylamino derivatives of dibenzofuran and dibenzothiophene when treated with secondary amines. We compare the physicochemical and spectral characteristics of the compounds obtained with the recyclization products of 1,3-dimethylbenzo[b]furo[2,3-c]- and 1,3-dimethylbenzo[b]thieno[2,3-c]pyrylium salts. L. M. Litvinenko Institute of Physical Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk 340114. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 182–185, February, 1998.     

Single stage synthesis of 2-alkylthio(seleno)-4-hetaryl-3-cyano-5,6,7,8-tetrahydroquinolines

Reaction of N-(1-cyclohexenyl)morpholine, hetarylmethylenecyanothio(seleno)acetamides, and alkyl halides gives 2-alkylthio(seleno)-4-hetaryl-3-cyano-5,6,7,8-tetrahydrothieno[2,3-b]quinolines.T. G. Shevchenko State University, Lugansk 348011. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1384–1390, October, 1997.     

Azabenzene chemisry. Part 2. Methylation of 2,3-dihydrooxazolo[4,5-b]pyridin-2-thione

Studies have been made on the reactions of 2,3-dihydrooxazolo[4,5-b]pyridin-2-thione and of its potassium and sodium salts with methylating agents under various conditions.See [1] for Part 1.Plant Substance Chemistry Institute, Uzbekistan Academy of Sciences, Tashkent 700170. Organic Nitrogen Technology Association, Interbioskrin, Moscow a/ya 218, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 87–89, January, 1999.     

Electrophilic substitution in benzo[b]thieno- and benzo[b]furo[2,3-c]pyridines. Use of the nuclear overhauser effect for determination of substitution position

The site of electrophilic substitution in benzo[b]thieno- and benzo[b]furo[2,3-c]pyridines has been determined using the nuclear Overhauser effect and by a method based on the difference in reactivity of the isomeric products.L. M. Litvinenko Institute for Physicoorganic Chemistry and Carbon Chemistry. Ukrainian Academy of Sciences, Donetsk 340114. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1199–1202, September, 1997.     

Synthesis and structure of some thienopyrimidine derivatives

A series of substituted thieno[2,3-d]pyrimidines was synthesized starting from ethyl-2-amino-4-isopropylthiophene-3-carboxlate. Reaction of 2-hydrazino-5-isopropyl-thieno[2,3-d]pyrimidin-4(3H)-one and its 3-methyl analogue with different reagents afforded thieno[2,3-d]triazolo[4,3-a]pyrimidines and thieno[3,2-e]triazolo[4,3-a]pyrimidines, beside open chain derivatives. Correspondence: Atef A. Hamed, Department of Chemistry, Faculty of Science, Menoufia University, Shebin El Koam, Egypt.     

An efficient synthesis of 2-cyano-2-phenyl-2,11b-dihydro-[1,3]oxazino[2,3-a]isoquinolines by reaction of isoquinoline with electron-deficient acetylenes in the presence of benzoylcyanide

Isoquinoline reacts with electron-deficient acetylenic compounds in the presence of benzoylcyanide to form 2-cyano-2-phenyl-2,11b-dihydro-[1,3]oxazino[2,3-a]isoquinolines in good yields. Correspondence: Issa Yavari, Chemistry Department, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran.     

Synthesis of pyrido[3′,2′:4,5]thieno[2,3-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-one derivatives

Some new pyrido[3′,2′:4,5]thieno[2,3-e]-[1,2,4]triazolo[4,3-a] pyrimidin-5(4H)-ones were prepared through heterocyclization of ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate with phenyl or ethyl isothiocyanate followed by nucleophilic displacement with hydrazine, and finally cyclocondensation with orthoesters. Correspondence: Abolghasem Davoodnia, Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad Branch, Mashhad 91735-413, Iran.     

Synthesis of derivatives of tetrazolo[1,5-a]- and oxazolo[4,5-b]pyrano(thiopyrano)[3,4-c]pyridines

Tetrazolo[1,5-a]- and oxazolo[4,5-b]pyrano(thiopyrano)[3,4-c]pyridines, which are new heterocyclic systems, have been synthesized from pyrano[3,4-c]pyridine derivatives.A. L. Mndzhoyan Institute of Fine Organic Chemistry, Armenian Academy of Sciences, Yerevan 375014. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1260–1262, September, 1997.     

Oxiranylβ-aminovinyl ketones. 6. Synthesis of N-substitutedcis-10-hydroxy-Δ2,3-

A method was developed for the synthesis of cis-10-hydrox-1methyl(aryl)-Δ ^2,3-octahhydro-4-quinolinones by the cyclization of 1-[cis-3-N-methyl(aryl)aminoacryloyl]-1,2-epoxycyclohexanes. For Communication 5, see [1]. Department of Organic Chemistry and the Chemistry of High-Molecular Compounds. Belarus State University, Minsk. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 225–228, February, 1998.     

A new synthetic route to 2-substituted naphtho[2,3-b]furan-4,9-dione2-Substituted Naphtho[2,3-b]furan-4,9-dione

4,9-Dimethoxynaphtho[2,3-b]furan 9 was obtained in 91% yield via the reductive methylation of naphtho[2,3-b]furan-4,9-dione 2 . After treatment of 9 with butyllithium, the mixture was allowed to react with N,N-dimethylacetamide, followed by oxidization with cerium(IV) diammonium nitrate to give 2-acetylnaphtho[2,3-b]furan-4,9-dione 1 . 2-Formylnaphtho[2,3-b]furan-4,9-dione 13 and 2-trimethylsilyl-naphtho[2,3-b]furan-4,9-dione 14 were also obtained from 9 by a similar method. The halodesilylations of 14 easily gave 2-iodonaphtho[2,3-b]furan-4,9-dione 16 , 2-bromonaphtho[2,3-b]furan-4,9-dione 17 , and 2-chloronaphtho[2,3-b]furan-4,9-dione 18 in 82%, and 93% and 83% yield, respectively. Furthermore, the nitrodesilylation of 14 gave 2-nitronaphtho[2,3-b]furan-4,9-dione 3 in 77% yield.     

Photochemical and thermal transformations of diazo derivatives of 1-aryloxy- and 1-arylthio-2-aminoanthraquinones

In the photochemical and thermal decomposition of diazonium derivatives of 1-aryloxy- and 1-arylthio-2-aminoanthraquinones in CH ₃ COOH and dioxane, high yields of intramolecular arylation products — anthra-[2, 1-d]-4-tert-butylbenzo-[b]-furan-and anthra-[2, 1-d]-4-tert-butylbenzo-[b]-thiophene-8,13-diones — are formed. It was established that 2-azo derivatives of 1-aryloxy- and 1-acyloxyanthraquinones synthesized on the basis of the diazonium salts are stable under photolysis conditions.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk 630090. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 582–585, March, 1992.     

Synthesis of new thiazolo[2,3-b]pyrimidine derivatives of pharmaceutical interest

2H-5-Amino-6-cyano-3,7-dioxothiazolo[2,3-b]pyrimidine was subjected to ring formation affording thiazolo[2,3-b]pyrimidine derivatives. 2H-5-Amino-6-cyano-3,7-dioxo-2-phenylmethylenethiazolo[2,3-b]pyrimidine was also subjected to ring formation affording pyrimido[4,5-d]-, pyrano[2,3-d]-, and pyrido[2,3-d]thiazolo[2,3-b]pyrimidine derivatives. 2-Anilinothiocarbonyl-3,9-dioxo-8-imino-7-phenyl-6-thioxothiazolo[2,3-b]pyrimido[4,5-d]pyrimidine and 8-amino-3,9-dioxo-6-thioxothiazolo[2,3-b]pyrimido[4,5-d]pyrimidine reacted with α-haloactive-methylene compounds to afford heterocyclic compounds containing two, fused and isolated, thiazole moieties, respectively.     

Synthesis of fused tetracycles from the nitration products of benzo[b]thieno[2,3-c]pyridines

The nitration products of benzo[b]thieno[2,3-c]pyridines were used in the synthesis of new fused tetracyclic heterocyclic systems, which are structural analogs of natural ellipticine and olivicine alkaloids. Closure of the pyridine ring gives products only with linear ring fusion. This behavior was explained using the steric strain-stability principle and complete optimization of the structure of these products with a PCMODEL program and MMX force field in conjunction with the -electron approximation.L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 340114 Donetsk, Ukraine. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 406–411, March, 1997.     

Halogenation of Imidazo[4,5-<Emphasis Type="Italic">b</Emphasis>]pyridin-2-one Derivatives

Chlorination and bromination of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one and its N-methyl-substituted derivatives in acetic acid at 90–95°C leads to formation of the corresponding 5,6-dichloro(dibromo)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones. Iodination of the same substrates with ICl under analogous conditions yields 6-iodo derivatives. Chlorination of 6-iodo-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one is accompanied by replacement of the iodine atom by chlorine with formation of 5,6-dichloro-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one. Bromination of 6-bromo- and 6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones gives 5,6-dibromo- and 5-bromo-6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, respectively.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 586–589.Original Russian Text Copyright © 2005 by Yutilov, Lopatinskaya, Smolyar, Gres’ko.     

Design,synthesis, and antimicrobial activity of fused triheterocyclic nitrogen systems involving tetrazolo[1,5-<Emphasis Type="Italic">b</Emphasis>][1,2,4]triazines [1]

Dehydrogenative cyclization of the 6-substituted 7-arylidenehydrazinotetrazolo[1,5-b][1,2,4]triazines derived from 6-methyl and 6-phenyl derivatives of 7-hydrazinotetrazolo[1,5-b][1,2,4]triazines and aromatic aldehydes gave the corresponding 6-substituted 9-aryl-[1,2,4]triazolo[4,3-d]tetrazolo-[1,5-b][1,2,4]triazines. The latter compounds were also obtained by an alternative route involving dehydrative cyclization of 6-methyl and 6-phenyl derivatives of 7-chlorotetrazolo[1,5-b][1,2,4]triazines with aromatic hydrazides through the isolable aroylhydrazino intermediates. Also, the triazolotetrazolotriazine rings were accomplished by one-pot cyclization of cyclic amidrazones with aromatic acid chlorides. The ditetrazolo[1,5-b:1′,5′-d][1,2,4]triazine systems were synthesized by cyclization of the former cyclic amidrazones with nitrous acid, or cyclic imidoyl chlorides with sodium azide. The bis-triazolotetrazolotriazine derivatives were synthesized by cyclization of two equivalents of each cyclic imidoyl chloride with acid dihydrazides through the isolable bis-hydrazide products. The antimicrobial activity of representative compounds was studied. Correspondence: Mamdouh A. M. Taha, Chemistry Department, Faculty of Science, Faiyoum University, Faiyoum 63514, Egypt.     

Acetylation of indolobenzo[b]furans,pyrrolocarbazole, pyrrolophenothiazine dioxide and pyrroloacridine under Vilsmeier reaction conditions

The course of the Vilsmeier acetylation of new heterocyclic systems, namely, indolo[4,5-d]-, indolo[6,5-d]-, indolo[5,6-d]-, indolo[5,4-d]benzo[b]furans, 3H-pyrrolo[2,3-c]carbazole, 3H-pyrrolo[2,3-c]pheno-thiazine 11,11-dioxide, and 3H-pyrrolo[2,3-c]acridine depends on the type of fusion of the pyrrole ring. Angular heterocycles are acetylated at the -position of the pyrrole ring, while linear heterocycles under analogues conditions give dimerization products with a substituent at the nitrogen atom of the hydrogenated part of the dimer molecule. 3H-Pyrrolo[2,3-c]phenothiazine 11,11-dioxide and 3H-pyrrolo[2,3-c]acridine are not acetylated under Vilsmeier reaction conditions.Georgian Technical University, 380075 Tbilisi, Georgia. D. E. Mendeleev Russian Chemical Engineering University, 125047 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1331–1336, October, 1996. Original article submitted August 19, 1996.