2‑(Methoxycarbonyl)ethyl as a Removable N‑Protecting Group: Synthesis of Indoloisoquinolinones by Pd(II)-Catalyzed Intramolecular Diamination of Alkynes

Pd­(II)-catalyzed double cyclization of 1,2-diarylethynes bearing an N-methyl-N-[2-(methoxycarbonyl)­ethyl]­amino and an aminocarbonyl group at the ortho positions of the two aromatic rings afforded the tetracyclic N-[2-(methoxycarbonyl)­ethyl]­indoloisoquinolinones in good to excellent yields. The...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 7; pp. 1750 - 1753
Main Authors Ha, Tu M, Yao, Bo, Wang, Qian, Zhu, Jieping
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.04.2015
Amer Chemical Soc
Subjects
alkynes
aromatic compounds
chemical reactions
Chemistry
Chemistry, Organic
moieties
nitrogen
Physical Sciences
Science & Technology
FUNCTIONALIZATION
ALPHA-ARYLATION
PALLADIUM-CATALYZED CYCLIZATION
EFFICIENT SYNTHESIS
TERMINAL ALKYNES
TANDEM REACTION
2,3-DISUBSTITUTED INDOLES
ORTHO-ALKYNYLANILINES
3-IODOINDOLES
DERIVATIVES
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.5b00526

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Summary:Pd­(II)-catalyzed double cyclization of 1,2-diarylethynes bearing an N-methyl-N-[2-(methoxycarbonyl)­ethyl]­amino and an aminocarbonyl group at the ortho positions of the two aromatic rings afforded the tetracyclic N-[2-(methoxycarbonyl)­ethyl]­indoloisoquinolinones in good to excellent yields. The N-[2-(methoxycarbonyl)­ethyl] group is readily removed under basic conditions (DBU, DMF, 120 °C) to afford the corresponding tetracycles with a free indolyl nitrogen in excellent yields. The 2-(methoxycarbonyl)­ethyl as a removable N-protecting group is illustrated in other Pd­(II)- and Pd(0)-catalyzed and selenium-mediated transformations.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.5b00526