Abstract
Some N-heterocyclic compounds such as pyrazino(2,3-f)(1,10)phenanthroline and dipyrido(3,2- a: 2',3'-c)phenazine can react with dialkyl acetylenedicarboxylate to give new helical compounds, which exhibit nonplanarity enforced by the crowding of the pyrrole rings.
Highlights
Addition reactions of acetylenic esters to nitrogen-containing heterocycles have been described by several research groups[1,2,3,4,5,6,7,8,9] and often lead to various products which may require great experimental skills for successful resolution.These polycyclic compounds are very interesting molecules from theoretical viewpoint and for their biological activity
For instance some pyrrolo[1,2-f]phenanthridines showed unique properties and be able to reduce the HIV-induced cytopathogenicity, and to stimulate the growth of the same MT cells at lower concentrations.[14]. An example of these reactions is the reaction between pyridine and dimethyl acetylenedicarboxylate in methanol, in which the indolizine 1,2,3-tricarboxylate 1 is isolated.15-20 1,10-phenanthroline derivatives can react with acetylenic esters to give dipyrrolo[1,2-a:2',1'
In order to provide further examples of this remarkable polycyclic compounds we examined the reaction of some phenanthroline derivatives such as pyrazino[2,3f][1,10]phenanthroline 4 and dipyrido[3,2-a:2',3'-c]phenazine 6 with acetylenic esters giving new helical compounds
Summary
Addition reactions of acetylenic esters to nitrogen-containing heterocycles have been described by several research groups[1,2,3,4,5,6,7,8,9] and often lead to various products which may require great experimental skills for successful resolution.These polycyclic compounds are very interesting molecules from theoretical viewpoint (synthesis, reactivity, stereochemistry, etc.) and for their biological activity. Addition reactions of acetylenic esters to nitrogen-containing heterocycles have been described by several research groups[1,2,3,4,5,6,7,8,9] and often lead to various products which may require great experimental skills for successful resolution. An example of these reactions is the reaction between pyridine and dimethyl acetylenedicarboxylate in methanol, in which the indolizine 1,2,3-tricarboxylate 1 is isolated.15-20 1,10-phenanthroline derivatives can react with acetylenic esters to give dipyrrolo[1,2-a:2',1'-
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callSimilar Papers
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
