Synthesis of substituted 3-amino[6,5-b]triazinoindoles

4-[(9-Methyl-as-triazino[6,5-b]indol-3-yl)amino]-2-methyl-2-butanol ( 13 ) and the corresponding 2-methyl-3-imino derivative 12 were synthesized and tested in vitro against Rhino 2 virus. The two compounds were more active than the known triazino[5,6-b]indole 4 . 2,9-Dimethyl-3-methoxy-9H-as-triazino[6,5-b]indolium tosylate ( 21 ) and the related 3-methylthio compound 9 were prepared. Quaternary 21 formed a pseudo base, 22a , whereas quaternary 9 did not form a pseudo base.     

4,9-Dihydrobenz[f]indole-4,9-dione derivatives synthesis and properties of 2,3,4,9-tetrahydrobenz[f]indole-2,4,9-triones and 2,3,4,9-tetrahydrobenz[f]indole-2,3,4,9-tetrones

Under the influence of amines, (3-chloro-1,4-naphthoquinon-2-yl)malonic ester is cyclized to 3-carbethoxy derivatives of 2,3,4,9-tetrahydrobenz[f]indole-2,4,9-trione, which were decarboxylated and then oxidized to 2,3,4,9-tetrahydrobenz[f]indole-2,3,4,9-tetrone derivatives. Methylation of 2,3,4,9-tetrahydrobenz[f]indole-2,4,9-triones leads to a mixture of O- and C-methyl derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 911–914, July, 1976.     

Investigation of 1,2,4-triazino [6,5-b]indole-derivatives

A method was worked out for the preparation of isatin -semicarbazone, the starting material for the synthesis of 3-hydroxy-l,2,4-triazacarbazoles, and the structure of the latter was refined. Nucleophilic exchange of 3-chloro-l,2,4-triazacarbazole (which was obtained for the first time) with amines, hydrazines, and arylhydrazines was studied.See [1] for communication I.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 855–857, June, 1972.     

Synthesis and properties of [1,4]diazepino[6,5-b]indoles

1-Aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole N-oxides were synthesized based on 3-(N"-aryl-N"-chloroacetyl)amino-2-formylindoles. Deoxidation of 2-oxo-1-phenyl-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole N-oxide afforded 1,2,3,6-tetrahydro- and 1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole derivatives. A new approach to the synthesis of pyrido[3,2-b]indole and pyrimido[5,4-b]indole derivatives was developed.     

5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类化合物的简便合成

报道了以2-甲(乙)基苯胺1a,1b为原料经Sandmeyer反应得到7-甲(乙)基靛红2a,2b;再以环境友好的聚乙二醇-400为溶剂,N-溴代丁二酰亚胺(NBS)为绿色溴代试剂对2a,2b进行5位溴代,得到5-溴-7-甲(乙)基靛红3a,3b;2a,2b,3a,3b进一步氮烃基化得到1-烃基-7-甲(乙)基靛红4a~4j和1-烃基-5-溴-7-甲(乙)基靛红5a~5j.2a,2b,3a,3b,4a~4j,5a~5j分别与硫代氨基脲,在以二氧六环为溶剂,碳酸钾存在的条件下回流反应,简便地合成了24种5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类杂环化合物6a~6x.大部分化合物未见文献报道,其结构经红外光谱、质谱、核磁氢谱(碳谱)和元素分析确认.     

17O and 11B NMR spectroscopic study of substituted benzo[d]-2,2-difluoro-1,3,2-oxoniaoxaboratins

¹⁷O NMR data are reported for 10 benzo[d]-2,2-difluoro-1,3,2-oxoniaoxaboratins derived from various ortho-hydroxyacetophenones and for 2,2-difluoro-1,3,2-oxoniaoxaboratins derived from related hydroxyacetyl naphthalenes and hydroxybenzophenones. The signal for the carbonyl-like oxygen for these compounds is substantially shielded and appears at 288 ± 22 δ. The single bonded oxygen signal for the 1,3,2-oxoniaoxaboratins appears at 122 ± 6 δ, except for the naphthalene analogs, whose signal appears at 146 ± 10 δ. The ¹¹B NMR signal for these compounds is insensitive to structural changes and appears at 0.85 ± 0.25 δ. © 1995 John Wiley & Sons, Inc.     

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.     

Synthesis of 3-phenyl- and 3-phenyl-1-methylimidazo [5, 1-b] benzoxazoles

Reduction of 2-benzoylbenzoxazole oxime gives 2-(-aminobenzyl) benzoxazole, converted to the formyl or acetyl derivative by treatment with, respectively, ethyl formate or acetic anhydride. Thiourea derivatives are obtained by treating 2-(-aminobenzyl) benzoxazole with arylisothiocyanates. Heating the above formyl or acetyl derivative with phosphorus oxychloride converts them to 3-phenyl- and 3-phenyl-1-methylimidazo [5, 1-b]-benzoxazole, which are representative members of a new tricyclic system. It did not prove possible to cyclize 1-[-(benzoxazolyl-2) benzyl]-3-phenylthiourea.     

Naphthindoles. 2. Naphtho[2,3-e]indole-4,9-diones and naphtho[2,3-f]indole-5,10-diones

The reactivity of naphtho[2,3-e]indole-4,9-dione and naphtho[2,3-f]indole-5,10-dione towards electrophiles (acylation, azocoupling, and the Mannich and Vilsmeier reactions) has been examined.For communication 1, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 783–786, June, 1989.     

Synthesis of novel 1,3-oxazino[6,5-b]indole-2,4-(3H,9H)-dione and 2H-1,3,5-oxadiazino[3,2-a]indole-2,4-(3H)-dione from oxindoles

Two novel tricyclic ring systems were designed as serine protease inhibitors and synthesized from oxindoles; the first series, 1,3-oxazino[6,5-b]indole-2,4-(3H,9H)-diones, were prepared from 2,3-dihydro-2-oxo-(1H)-indole-3-carboxamides and phosgene in tetrahydrofuran with triethylamine. The second, a 2H-1,3,5-oxadiazino[3,2-a]indole-2,4-(3H)-dione was made using a similar cyclization on 2,3-dihydro-2-oxo-N-phenyl-(1H)-indole-1-carboxamide.     

A Convenient Preparation of 8-Ethyl-4,9-dihydro-3H-pyrano[3,4-b]indole-1-one,Key Intermediate of the Antiinflammatory Agent Etodolac

A facile synthesis of 8-ethyl-4,9-dihydro-3H-pyrano [3,4-b]indole-1-one 5 is described which features the condensation of hydrazines with 2-oxo-5-hydroxypentanoic acid, followed by Fischer Cyclization of these adducts.     

Synthesis of derivatives of naphtho[2,3-b]furan-4,9-dione

The reaction of 2,3-dichloro-1,4-naphthoquinone with ketoenols has been studied. A series of substituted naphtho[2,3-b]furan-4,9-quinones has been synthesized and some of their reactions have been studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 7, pp. 867–870, July, 1970.     

The reactions of 2,2-difluoro-4-methylnaphtho[l,2-e]-1,3,2-dioxaborin and its [2,1-e]isomer with N,N-dimethylformamide

The title compounds react with dimethylformamide in acetic anhydride to give dimethylamino-vinyl derivatives which, on treatment with base, yield benzochroman-4-ones. The [1,2-e] isomer reacts with the Vilsmeier complex to give 3-formylbenzo[f]chrom-4-one and 9-hydroxy-1-phenalenone, and the [2,1-e]isomer gives 3-formylbenzo[h]chrom-4-one.     

Acyl Indoles. III. The synthesis of [1,4] diazcpino [6,5-b ] indoles

The synthesis of 1,3,4,6-letrahydro-6-metliy]-2H,5H-[1,4]diazepino[6,5-b] indole-2,5-diones and 5-phenyl-3,6-dihydro[1,4]diazepino[6,5-b ]indole-2(lH)one is described. Also detailed is the, preparation of a 3-amino-2-benzoylindole.     

A new method for the synthesis of [1,4]diazepino[6,5-b]indole derivatives

Reactions of 3-[(N-aryl-N-chloroacetyl)amino]-2-formylindoles with substituted anilines gave 1,4-diaryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indol-4-ium chlorides and those with 4-aminopyridine yielded 4-amino-1-(1-aryl-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indol-3-yl)pyridinium chlorides. Reduction of 1,2,3,6-tetrahydrodiazepinoindol-4-ium chlorides afforded the corresponding hexahydro derivatives. An alternative synthesis of 1-(4-nitrophenyl)-3-oxo-4-phenyl-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole from 3-[N-(4-nitrophenyl)amino]-2-[(phenylimino)methyl]indole was developed. The method involves the following sequence of transformations: reduction, chloroacetylation, and intramolecular alkylation. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2193–2199, December, 2006.     

A short-step synthesis of naphtho[2,3-b]furan-4,9-dione

Phthalic anhydride in THF was added to 3-lithiofuran 2 in THF to give 3,3-di-(3-furyl)-1,3-dihy-droisobenzofuran-1-one 4 . On the other hand, 2 in THF was added to phthalic anhydride in THF to give 2-(3-furanoyl)benzoic acid 3 by the inverse addition method. Further, the parent naphtho[2,3-b]furan-4,9-dione 1 was obtained from the reaction of 3 with two equimolar amounts of LDA.