6521-33-1Relevant articles and documents
Transition metal-free one-pot synthesis of 2-substituted 3-carboxy-4-quinolone and chromone derivatives
Lin, Jian-Ping,Long, Ya-Qiu
, p. 5313 - 5315 (2013/06/27)
A novel one-pot synthesis of the 2-substituted 3-carboxy-4-quinolone/ chromone derivatives from readily available 3-oxo-3-arylpropanoates and amides/acyl chlorides is reported, without any transition metal aid. The Royal Society of Chemistry 2013.
Synthesis of some novel imidate derivatives of thiophene and furan: Investigations of their metallation properties and some synthetic applications
Barcock, Richard A.,Chadwick, Derek J.,Storr, Richard C.,Fuller, Lance S.,Young, John H.
, p. 4149 - 4166 (2007/10/02)
Methyl N-methyl and methyl N-(2,4,6-trimethyl)phenyl-2-carboximidates of thiophene and furan have been synthesized in excellent yields by the reactions of sodium methoxide in methanol with the corresponding N-methyl- and N-(2,4,6-trimethyl)phenyl-2-carboxymidoyl chlorides, which in turn, were obtained from their respective secondary amides by refluxing in neat thionyl chloride. A thorough investigation into the directed lithiation properties of the these heteroaryl-2-imidates with various lithiating agents, solvents, and reaction conditions revealed almost exclusive C5-lithiation. This regioselectivity is in contrast to the C3-lithiation reported for the oxazolino functionality (a cyclic imidate). The synthetic utility of the C5-lithiated intermediate of methyl N-methyl-thiophene-2-carboximidate with various electrophiles is demonstrated. C3-Lithiation has been effected in the case of methyl N-methylthiophene-2-carboximidate when the C5-position is blocked with a removable trimethylsilyl group. Methyl thiophene-2-carboximidate, an N-unsubstituted imidate, was found to eliminate methoxide ion and undergo subsequent C5-lithiation to give 5-lithiothiophene-2-carbonitrile with LDA. n-Butyllithium gave rise predominantly to products resulting from nucleophilic addition to the nitrile group.