CuI-Catalyzed Selective 3-Alkylation of Indoles with N-Tosylhydrazones and the I-2-Mediated Further Cyclization to Chromeno[2,3-b]Indoles

The CuI-catalyzed reaction of indoles with N-tosylhydrazones derived from the ortho-/para-hydroxybenzaldhydes affords selectively the C-3 alkylated products rather than the N-alkylated products. In addition, the I-2-mediated cyclization of the generated C-3 alkylated products allows the concise synt...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 360; no. 13; pp. 2440 - 2445
Main Authors Miao, Chun-Bao, Sun, Yan-Fang, Wu, He, Sun, Xiao-Qiang, Yang, Hai-Tao
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 04.07.2018
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
indole
QUINONE METHIDES
ALKYLATION
STRATEGY
BOND FORMATION
chromeno[2,3-b]indole
FUNCTIONALIZATION
OXYGEN
N-tosylhydrazone
CuI
H INSERTION
iodine
GENERATION
DERIVATIVES
ACCESS
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Summary:The CuI-catalyzed reaction of indoles with N-tosylhydrazones derived from the ortho-/para-hydroxybenzaldhydes affords selectively the C-3 alkylated products rather than the N-alkylated products. In addition, the I-2-mediated cyclization of the generated C-3 alkylated products allows the concise synthesis of chromeno[2,3-b]indole derivatives.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800206