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 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.


Published in:
Organic Letters, 17, 7, 1750-1753
Year:
2015
Publisher:
Washington, Amer Chemical Soc
ISSN:
1523-7052
Laboratories:




 Record created 2015-04-08, last modified 2018-09-13


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