Synthesis of 3-[5-anilino-(2,3-d)-dioxole-1,3]-1-oxo-1,3-dihydro-2-benzofurane

A microscale synthesis (500 mg) of the product 3-[5-anilino-(2,3-d)-dioxole-1,3]-1-oxo-1, 3-dihydro-2-benzofurane (COR.01.126) is described. This method, which requires only four steps, is principally available for the ¹⁴C-labeled synthesis with labeled phthalic anhydride as starting material.     

Synthesis of 5,6-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-f][1,4]diazepines

The reduction of 1-[3-(thienyl-2-carbonitrile)]pyrrole, formed by condensation of 3-aminothiophene-2-carbonitrile with 2,5-dimethoxytetrahydrofuran, gave 1-[3-(thienyl-2-aminomethyl)]pyrrole. This compound was found to be a convenient intermediate for the preparation of 4-aryl-5,6-dihydro-4H-pyrrolo[1,2-a]thieno-[2,3-f][1,4]diazepines which was accomplished by two different synthetic routes.     

Synthesis of new 1,3-disubstituted-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines

1,3-Disubstituted-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines were prepared through the ring-closure reactions of the aminobenzylnaphthols with substituted aryl- and heteroarylaldehydes.     

Synthesis of furo[2,3-f]- and furo[3,2-e]indole derivatives

Two compounds — the diethylamides of 1,2-dimethyl-3-carbethoxy-6-carboxyfuro[2,3-f]- and 1,2-dimethyl-3-carbethoxy-5-carboxvfuro[3,2-e]indoles — are formed in the reaction of 1,2-dimethyl-3-carbethoxy-5-hydroxyacetic acid (I) with dimethylformamide and phosphorus oxychloride as a result of subsequent intramolecular cyclization of the intermediates. This constitutes evidence for formylation of the starting acid in the 6 and 4 positions. Formylation of the ethyl ester of acid I gives only the 6-formyl derivative, the intramolecular cyclization of which under the influence of sodium ethoxide gives 1,2-dimethyl-3,6-dicarbethoxyfuro[2,3-f]-indole. Hydrolysis of the latter with alcoholic alkali gives the corresponding dicarboxylic acid. The structures of the synthesized compounds were confirmed by the PMR, IR, and mass spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 766–769, June, 1977.     

Synthesis and study of 5a,6-dihydro-12H-indolo[2,1-b][1,3]-benzoxazines

Reaction of 2,3,3-trimethyl-, 2,3,3,5- and 2,3,3,7-tetramethyl-3H-indoles with 4-nitro-2-chloromethylphenol has given the 5a,6-dihydro-12H-indolo-[2,1-b][1,3]-benzoxazines, which have been examined for ring-chain interconversion by NMR spectroscopy. Treatment of 5a,6-dihydro-12H-indolo[2,1-b][1,3]benzoxazines with either perchloric acid or potassium hydroxide results in opening of the dihydrooxazine ring with the formation of indole derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 672–676, May, 1989.     

2,3-二芳基-1,3-苯并噁嗪的合成及杀菌活性

在三甲基氯硅烷(TMSCl)的催化作用下,取代苯甲醛与邻(芳胺甲基)苯酚经N杂缩醛化反应生成了一系列2,3-二芳基-1,3-苯并噁嗪类化合物。 目标化合物的结构用IR、¹H NMR、¹³C NMR和元素分析等技术手段进行了表征。 对所合成的化合物进行了初步杀菌活性测试,部分表现出良好的杀菌活性,化合物6e对菌核病菌的抑制活性为79.0%,化合物6a和6d均为74.8%,化合物6e对灰霉病菌的抑制活性为77.9%。     

7,8-二氢-6,6-二甲基-7,8-环氧-6氢-吡喃[2,3-f]苯并-2,1,3-恶二唑的合成

本文给出了一条较好的制备7,8-二氢-6,6-二甲基-7,8-环氧-6氢-吡喃[2,3-f]苯并-2,1,3-恶二唑的合成路线，即由对乙酰氨基苯酚经酯化、Fries重排、环合、还原、脱水、硝化、脱酰基、氧化、脱氧和催化环氧化等反应制得标题化合物，其结构经元素分析和光谱数据确证。     

Pyrroloindoles. 15. Synthesis of tryptamine analogs. 6,7-dihydro-3-(2-phthalimidoethyl)-1h,5h-pyrrolo[2,3-f]indole and 3-(2-phthalimidoethyl)-1H,5H-pyrrolo[2,3-f]indole

Diazotization of 1-acetyl-S-aminoindoline and reaction of the diazonium salt with ethyl -acetyl--phthalimidovalerate gave the 1-acetyl-5-iruiolhgl hydrazone of ethyl -keto--phthalimidovalerate. Cyclization of the hydrazone and subsequent hydrolysis, decarboxylation, and dehydrogenation of the pyrroloiruloline gave the corresponding tryptamines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 209–212, February, 1994. Original article submitted July 20, 1993.     

Construction of functionalized 2,3-dihydro-1,4-benzoxazines via [5 + 1] annulations of 2-halo-1,3-dicarbonyl compounds with imines

A series of functionalized 2,3-dihydro-1,4-benzoxazines were obtained in moderate to excellent yields via domino [5 + 1] annulations of 2-halo-1,3-dicarbonyl compounds 2 with imines 1 under mild conditions and the application of this method in the synthesis of bioactive analogues, such as functionalized tetracyclic-1,4-benzoxazines which contain two new heterocyclic rings and one quaternary carbon center has also been developed.     

Synthesis and fungicidal activity of novel 2,3-disubstituted-1,3-benzoxazines

A series of new 2,3-disubstituted-3,4-dihydro-2H-1,3-benzoxazines were prepared in moderate to excellent yields by aza-acetalizations of aromatic aldehydes with 2-(N-substituted aminomethyl)phenols in the presence of TMSCl. Their structures were confirmed by IR, 1H-NMR, 13C-NMR, MS and elemental analysis. The fungicidal activities of the target compounds were preliminarily evaluated, and some compounds exhibited good activity against Rhizoctonia solani.     

Substituted 1,10b-dihydro-5H-pyrazolo[1,5-c]-1,3-benzoxazines

A study was made of the reaction of 3-phenyl-5-(2-hydroxyphenyl)-1H-2-pyrazoline with various aldehydes and ketones, which results in the formation of derivatives of 1,10b-dihydro-5H-pyrazolo[1,5-c]-1,3-benzoxazine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1131–1136, August, 1991.     

Aryl-substituted 1,10b-dihydro-5H-pyrazolo[1,5-c]-1,3-benzoxazines

Substituted 1,10b-dihydro-5H-pyrazolo[1,5-c] 1,3-benzoxazines have been obtained by condensation of 5-(2-hydroxyphenyl)-3-phenylpyrazole with aromatic aldehydes. The detailed structure of the compounds obtained has been elucidated from their¹H NMR spectra by application of the nuclear Overhauser effect and the conclusions have been confirmed by an X-ray diffraction study.Khar'kov State University, Khar'kov 310077, Ukraine Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, 805–810, June, 1999.     

Synthesis of [1,3]Thiazolo[2,3-i]purinium Systems

Russian Journal of Organic Chemistry - The alkylation of purine-6-thiol with methallyl chloride and propargyl bromide in aqueous alcohol in the presence of alkali gave...     

Synthesis of 2,6-disubstituted-7,8-dihydro-6H-pyrano[2,3-6]pyrazines

A straightforward synthesis of a 2,6-disubstituted-7,8-dihydro-6H-pyrano[2,3-6]pyrazine is described. The synthesis relies on a versatile dichloropyrazine–aldehyde intermediate and an olefination partner.     

Derivatives of 3,4-dihydro-2H-benzo[b][1,4]dioxepin. Preparation of 7,8-dihydro-6H-[1,4]dioxepino[2,3-f]-2,1,3-benzoxadiazole 1-oxide

A novel annelated benzofuroxan 4 and a benzofurazan 4a have been prepared in good yields. Nitration of 5 afforded both trinitro derivatives 6 and 7 . Low temperature nmr spectroscopy was applied on compound 4 and the value ΔG* is reported.     

The Synthesis of 3-Acyl-2,3-dihydro-2,2-dimethyl-1,3-thiazoles

Acylation of 2,5-dihydro-2,2-dimethyl-1,3-thiazoles leads to 3-acyl-2,3-dihydro-2,2-dimethyl-1,3-thiazoles as potential starting materials for the total synthesis of racemic cephalosporins.