Open AccessThe dipolar cycloaddition of methyl acrylate to 1,5,6‐trimethyl‐3‐oxidopyrazinium
Author(s) -
Helliwell Madeleine,
You Yun,
Joule John A.
Publication year - 2006
Publication title -
acta crystallographica section e
Language(s) - English
Resource type - Journals
ISSN - 1600-5368
DOI - 10.1107/s1600536806007501
Subject(s) - methyl acrylate , octane , deprotonation , chemistry , cycloaddition , salt (chemistry) , medicinal chemistry , 1,3 dipolar cycloaddition , acrylate , methylene , carboxylate , organic chemistry , catalysis , polymer , ion , monomer , copolymer
5,6‐Dimethylpyrazin‐2‐one reacts with iodomethane to give a quaternary salt, deprotonation of which liberates a 3‐oxidopyrazinium which undergoes a 1,3‐dipolar cycloaddition with methyl acrylate to form methyl 5,8‐dimethyl‐4‐methylene‐2‐oxo‐3,8‐diazabicyclo[3.2.1]octane‐6‐ exo ‐carboxylate, C 11 H 16 N 2 O 3 , as the major product.