Cyclization of free radicals at the C-7 position of ethyl indole-2-carboxylate derivatives: an entry to a new class of Duocarmycin Analogues

Naim H Al-Said; Khaled Q Shawakfeh; Wasim N Abdullah

doi:10.3390/10121446

Cyclization of free radicals at the C-7 position of ethyl indole-2-carboxylate derivatives: an entry to a new class of Duocarmycin Analogues

Molecules. 2005 Dec 31;10(12):1446-57. doi: 10.3390/10121446.

Authors

Naim H Al-Said¹, Khaled Q Shawakfeh, Wasim N Abdullah

Affiliation

¹ Department of Applied Chemical Science, Jordan University of Science and Technology, P.O. Box 3030, Irbid 22110, Jordan. naim@just.edu.jo

Abstract

Aryl free-radicals generated at the C-7 position of ethyl indole-2-carboxylates bearing N-allyl and propargylic groups triggered intramolecular cyclizations to furnish a new class of Duocarmycin analogues, formal ethyl pyrrolo[3,2,1-ij]quinoline-2- carboxylate derivatives, through the less favorable 6-endo-trig cyclization mode.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylating Agents / chemical synthesis*
Alkylating Agents / chemistry
Cyclization
Duocarmycins
Free Radicals / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry*
Molecular Structure
Pyrroles / chemical synthesis
Pyrroles / chemistry
Quinolines / chemistry

Substances

Alkylating Agents
Duocarmycins
Free Radicals
Indoles
Pyrroles
Quinolines
indole-2-carboxylate
pyrroloquinoline
duocarmycin SA