ChemInform Abstract: Phenanthridine or Isoquinoline Are Good Reagents for the Synthesis of Enamino Esters.

Abstract

Phenanthridine or Isoquinoline Are Good Reagents for the Synthesis of Enamino Esters. -A new method to synthesize a novel class of heterocyclic derivatives, e.g. (IV), (VI), and (IX) is presented. Nucleophiles, e.g. 5-nitroindazole, benzoxazole or carbazole can also be used for the reaction. -(NASSIRI, M.; HEYDARI, R.; HAZERI, N.; HABIBI-KHORASSANI, S. M.; MAGHSOODLOU*, M. T.; MILANI, F. J.; J. Chem. Res. 34 (2010) 7, 365-369, http://dx.

A three-component reaction between azaarenes (phenanthridine, quinoline or isoquinoline), acetylenic esters and phenol derivatives

“…In addition, product 4a displayed 13 C NMR resonances at δ = 63.14, 109.35 and 123.90 ppm, respectively for the NCHC, N-CH=CH-CO 2 CH 2 CH 3 , and N-CH=CH-CO 2 CH 2 CH 3 units. [22][23][24] The carbonyl group resonance in the 13 C NMR spectrum of 4a appear at δ = 168.35 ppm. The 1 H and 13 C NMR spectra of compounds 4b, 8c-e and 12f-g are similar to those of 4a.…”

“…The reaction between azaarenes (phenanthridine 1, isoquinoline 5 or quinoline 9) and acetylenic esters 2, 6 or 10 as a Michael acceptor [19][20][21][22][23][24] was undertaken in the presence of phenol derivatives (2,5-dimethylphenol, 2,4-di-tert-butylphenol, 4methylphenol and 4-chloro-3,5-dimethylphenol) at ambient temperature (see Scheme 2 and Table 1). Reactions were carried out by first mixing the phenanthridine, isoquinoline or quinoline and phenol derivatives and then the acetylenic ester was added slowly.…”

A Mild and Efficient Method to Functionalize Azines (Quinoline, Isoquinoline, and Phenanthridine) Using Acetylenic Esters and Heterocyclic NH or 1,3‐Dicarbonyl Compounds

“…The reaction of azines (phenanthridine 1 , isoquinoline 5 , or quinoline 9 ) with acetylenic esters 2 , 6 , or 10 as a Michael acceptor was undertaken in the presence of heterocyclic NH compounds (benzotriazole, 2‐methylbenzimidazole, maleimide, indole, 2‐methyl indole, 2‐benzoxazolinone, and 6‐chlorobenzoxazo‐linone) or 1,3‐dicarbonyl compound such as 5,5‐dimethyl‐1,3‐cyclohexadione at RT. Reactions were carried out by first mixing the phenanthridine, quinoline, or isoquinoline and heterocyclic NH or 1,3‐dicarbonyl compounds, and then, the acetylenic ester was added slowly.…”