Synthesis of 1,2,3,4-Tetrahydroeudistomin U Derivatives and Preliminary<i>In Vitro</i>. Antitumor Evaluation

Zheng, Jianbin; Zhang, Zhiwen; Zhao, Lingling; Sha, Xianyi; Dong, Xiaochun; Ren, Wen Xiu

doi:10.1080/13880200701741120

Cited by 5 publications

(3 citation statements)

References 9 publications

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“…Under MW agitation at 100 ο C, the reaction time could be decreased from 4 h to 30 min ( Table 2). The synthesis of 9a has already been achieved [22][23][24] from 1H-indole-3-ethanamine and 1Hindole-3-carboxaldehyde via Pictet-Spengler condensation. The main advantage of our method is the application of indole instead of indole-3-carboxaldehyde.…”

Section: Resultsmentioning

confidence: 99%

One-pot α-arylation of β-carboline with Indole and Naphthol Derivatives

Sas

Szatmári

Fülöp

2016

COS

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4,9-Dihydro-3H-β-carboline and 6-methoxy-4,9-dihydro-3H-β-carboline were subjected to catalyst-free onepot α-arylation with 1 or 2-naphthol, 6-hydroxyquinoline or 5-hydroxyisoquinoline as N-containing analogues via direct aza-Friedel-Crafts reactions. The procedure was then extended to other electron-rich aromatic compounds, such as indole or indole-2-carboxylic acid, to yield new indole γ-amino acid derivatives containing β-carboline skeleton. All the reactions were performed both under neat conditions and with microwave irradiation. The reaction of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and benzaldehyde with 1-naphthol as nucleophile led to the formation of the N-alkylated compound as a single product, whereas the reaction with 2-resulted in the two possible α-arylated/N-alkylated products, in a ratio depending on the reaction conditions.

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Section: Resultsmentioning

confidence: 99%

One-pot α-arylation of β-carboline with Indole and Naphthol Derivatives

Sas

Szatmári

Fülöp

2016

COS

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“…, when 6,7-dihydrothieno[3,2-c]pyridine (85) was reacted either with 20a or with 79. From the results inTable 15(entries 8-11), it can be concluded that 85 has a higher reactivity with indolederivatives as compared with 4,6-dihydro-3H-benz[c]azepine(84).…”

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confidence: 99%

“…When the reaction was repeated under MW agitation at 100 ο C, the reaction time could be decreased from 4 h to 30 min(Table 16). The synthesis of 93a was earlier achieved[82][83][84] from 1H-indole-3-ethanamine and 1H-indole-3-carboxaldehyde via Pictet-Spengler condensation. The main advantage of our method is the application of indole derivatives instead of indole-3-carboxaldehyde, the direct α-arylation of partially saturated β-carbolines with electronrich aromatic compounds opening up new areas of diversity for this reaction.…”

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confidence: 99%