Letters in Organic Chemistry

Author(s): Julia V. Hernandez-Madrigal, Armando Pineda-Contreras, Oscar F. Vazquez-Vuelvas, Mikhail A. Tlenkopatchev, Hector Garcia-Ortega, Ruben Gavino-Ramirez and Zeferino Gomez-Sandoval

DOI: 10.2174/157017811795371458

Synthesis of Novel Pyridinium Betaine Precursors from exo-Norbornene Dicarboximides

Page: [249 - 257] Pages: 9

  • * (Excluding Mailing and Handling)

Abstract

N-heterocyclic norbornene Dicarboximides were synthesized by reacting the exo-norbornene-5,6-dicarboxylic anhydride with 2-, 3-, and 4-aminopyridine. The amides resulting from 3 and 4-aminopyridine derivatives were converted into the corresponding betaines via Menshutkin reaction using ethyl-bromoacetate. The chemical structures of the obtained products were confirmed by FT-IR and 1H and 13C NMR spectroscopy, EA and MS as well as by calculation of 1H and 13C NMR chemical shifts using the GIAO method (PW91/6-311G++ (3df, 3pd) approximation by GAUSSIAN and PW91/IGLO-III approximation by deMon2k).

Keywords: Betaine precursors, dicarboximides, Menshutkin reaction, norbornene, pyridinium, zwitterions, anhydride, zwitterionic, solvatochromism