Author:
Potáček Milan,Topinka Tomáš,Dostál Jiří,Marek Jaromír
Abstract
Azomethine ylides generated from 5-(alkoxycarbonylmethyl) phenanthridinium cations I were used in the 1,3-dipolar cycloadditions with dimethyl acetylenedicarboxylate as dipolarophile. The cycloadducts II were found to be very unstable species and readily oxidized to fully aromatic pyrrolo[1,2-f]phenanthridines III. Their structure was compared with the compounds formed by the oxidation of cycloadducts IV of the same ylide with dimethyl fumarate and maleate. In both cases pyrrolines V were found as intermediates. The structure of the products was determined by NMR and MS as well as by X-ray analysis.
Publisher
Institute of Organic Chemistry & Biochemistry
Cited by
11 articles.
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1. Isoquinolino[4,3,2-de]phenanthridine: synthesis and its use in 1,3-dipolar cycloadditions to form nitrogen-containing polyaromatic hydrocarbons;Chemical Communications;2015
2. Efficient Synthesis of Pyrrolo[1,2-f]phenanthridine Derivatives via Dipolar Cycloaddition of Phenanthridine, Activated Acetylenes, and Ethyl Bromopyruvate;Synthetic Communications;2013-10-11
3. ChemInform Abstract: Phenanthridinium-Based Azomethine Ylides in 1,3-Dipolar Cycloaddition with Dimethyl Acetylenedicarboxylate.;ChemInform;2010-08-17
4. A Novel One-Pot, Three-Component Access to Hexahydropyrrolo[2,1-a]isoquinolines by an Alkylation-Dehydrohalogenation-1,3-Dipolar Cycloaddition Sequence;Synthesis;2005
5. Azomethine Ylides in Organic Synthesis;Current Organic Chemistry;2003-07-01