TOSYLATE OF ETHYL 3-AMINO-2-PHENYLIODONIOCROTONATE: SYNTHESIS, CRYSTAL STRUCTURE, AND SYNTHESIS OF HETEROCYCLIC COMPOUNDS BASED ON IT

Abstract

Ethyl 3-aminocrotonate, when reacted with hydroxy(tosyloxy)iodobenzene, forms the tosylate of ethyl 3‑amino-2-phenyliodoniocrotonate which crystallizes well in up to 80% yield. X-ray analysis confirms the structure of the phenyliodonium salt, revealing intramolecular and unusual intermolecular hydrogen bonds, stabilizing the compound in the crystalline state. Reaction with pyridine, its 4-substituted derivatives, and 4,4'-bipyridine yields tosylates of 2-pyridinio-substituted ethyl 3-aminocrotonates. ¹H NMR and IR spectra support formation of an intramolecular hydrogen bond for the E-isomer, and iodonium salts in the case of pyridinium salts for the Z-isomer. The UV spectra of the pyridinium salts show an intramolecular charge transfer band.

Authors: O. Neilands and S. V. Belyakov.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (6), pp 672-678

http://link.springer.com/article/10.1007/BF02297675