- Preparation method of compound 5,6-dihydroxy indoline and halogen acid salts thereof
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The invention relates to a preparation method of a compound 5,6-dihydroxy indoline and halogen acid salts thereof. Phenylethylamine SM-0 sold in the market is used as a raw material and firstly reactswith acyl chloride to obtain amide SM-1; amide SM-1 rea
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Paragraph 0059-0062
(2018/04/01)
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- Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams
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Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright
- Harada, Rika,Nishida, Naoto,Uchiito, Shiho,Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Masao, Tokuda,Ohkuma, Takeshi,Orito, Kazuhiko
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experimental part
p. 366 - 379
(2012/02/04)
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- Studies on the Syntheses of Heterocyclic Compounds. Part 865. A Novel Synthesis of Indole Derivatives by Intramolecular Nucleophilic Aromatic Substitution
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Cyclisation of N-(2-bromo-4,5-dimethoxyphenethyl)acetamide (6) afforded 1-acetyl-2,3-dihydro-5,6-dimethoxy-1H-indole (13) by intramolecular nucleophilic aromatic substitution using sodium hydride and cuprous halide in dimethylformamide.The dihydroindoles (14), (15), and (16) were also synthesised from the corresponding amides (8) and (10) and the carbamate (12) in a similar manner.The dihydroindoles (13), (14), and (16) were converted into the indoles (20) and (21) in excellent yield by oxidation and subsequent alkaline hydrolysis.The 2-oxindoles (26) and (27) were also prepared under similar reaction condition from the phenylacetamide (24) and (25).
- Kametani, Tetsuji,Ohsawa, Tatsushi,Ihara, Masataka
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p. 290 - 294
(2007/10/02)
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- A NOVEL SYNTHESIS OF INDOLE DERIVATIVES
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1-Acetyl-2,3-dihydro-5,6-dimethoxy-1H-indole (13) was synthesized by cyclization of N-(2-bromo-4,5-dimethoxyphenethyl)acetamide (6) using sodium hydride and cuprous halide in dimethylformamide.Indoles (14,15 and 16) were prepared in a similar manner from
- Kametani, Tetsuji,Ohsawa, Tatsushi,Ihara, Masataka
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p. 277 - 280
(2007/10/02)
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