Reactions of 2,2-pentamethylene-1,3-dioxan-4,6-dione with triethyl orthoformate and aromatic amines

Abstract

Condensation of 2,2-pentamethylene-1,3-dioxane-4,6-dione with tri-Et orthoformate and a series of substituted anilines proceeds smoothly to give 39.7-96.9% the corresponding anils I (R = halo, NO2, Me, etc.). Lack of the characteristic peak of hydroxy group in IR and appearance of the proton on nitrogen atom in down field of 1H NMR indicate that the most possible structure of the anil is the intermol. hydrogen-bonded form.

Key words: REACTION MECHANISM, CONDENSATION REACTION, INFRARED SPECTROPHOTOMETRY, ETHYL ESTER, FORMIC ACID P, MASS SPECTROGRAPHY, DIKETONE, ELEMENTAL ANALYSIS, CARBOXYLIC ACID ESTER, PROTON MAGNETIC RESONANCE SPECTROMETRY

CLC Number:

O621

Cite this article

XU FUPEI;DING WEIYU;DA BAOLIN. Reactions of 2,2-pentamethylene-1,3-dioxan-4,6-dione with triethyl orthoformate and aromatic amines[J]. Chin. J. Org. Chem., 1991, 11(3): 318-321.

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