2-Acylcyclohexane-1: 3-diones. Part II. 2-Formyl-, 2-propionyl-, 2-iso-butyryl-, and 2-phenylcarbamoyl-cyclohexane-1: 3-dione, and their conversion into phenanthridines

Abstract

Rogers avtd Smith. 341 2-Acylcyclohexane-l : 3-diones. Part I P 2-Formyl-, 2-PropionyE-, 2-iso-Butyryl-, and 2-Phenylmrbamoyl-cyclohexane-l : %&one, and their Conversion into Phenant h r id ines.* " 2-Acetylcyrlohexane-1 : 3-dione," Smith, J . , 1953, 803, is regarded as Part 1 of this series.

Primary tritium and deuterium isotope effects on chemical shifts of compounds having an intramolecular hydrogen bond

“…1. Apart from sharing this feature the compounds are from various classes, such as nitroso (39) and azo-hydrazo (40)(41)(42) compounds, enamines (43)(44)(45), amides (12,46), thioamides (48)(49)(50)(51), carboxylic acids (38),ˇ-keto esters (10,11,13),ˇ-diketones (1-6, 14, 15),˛-acetyl-ˇ-diketones (7-9, 37, 47),ˇ-thioxoketones (52)(53)(54), hydroxyanthraquinones (16-18, 21, 22), hydroxynaphthoquinones (19,20,23,24), o-hydroxy aromatic ketones (25-30, 32-36, 37, 55) and esters (31). This range of compounds covers intramolecular hydrogen-bonded systems with oxygen, nitrogen and sulfur in the donors and acceptor functions.…”

Using Chou’s 5-Step Rule to Evaluate the Stability of Tautomers: Susceptibility of 2-[(Phenylimino)-methyl]-cyclohexane-1,3-diones to Tautomerization Based on the Calculated Gibbs Free Energies

“…Tautomeric preferences of 2-(anilinemethylidene)cyclohexane-1,3-dione were studied for the first time almost sixty years ago [54]. These compounds reveal interesting biological properties [55].…”

Metal- and Base-Free Combinatorial Reaction for C-Acylation of 1,3-Diketo Compounds in Vegetable Oil: The Effect of Natural Oil

“…1 Since then, these compounds have attracted attention because 1,3,3′ tricarbonyl derivatives inhibit p-hydroxyphenylpyruvate dioxygenase, which is an important enzyme for herbicide research. 2 Moreover, tricarbonyl compounds are a vital intermediate for synthesis of pharmaceutically important compounds, e.g., Rimonabant and 5-deazaaminopterin.…”

“…C-acylation of 1,3-diketo compounds to obtain 1,3,3′tricarbonyl compounds has been performed by reactions between 1,3-diketo compounds and acid anhydrides in the presence of a base as early as 1955. 1 Since then, these compounds have attracted attention because 1,3,3′ tricarbonyl derivatives inhibit p-hydroxyphenylpyruvate dioxygenase, which is an important enzyme for herbicide research. 2 Moreover, tricarbonyl compounds are a vital intermediate for synthesis of pharmaceutically important compounds, e.g., Rimonabant and 5-deazaaminopterin.…”

“…(a)1 H NMR spectrum of the reaction in xylene for 24 h for 4aa (crude NMR). (b) 1 H NMR spectrum for the reaction in corn oil for 15 min for 4aa (crude NMR).…”