R. A. Gadzhili, R. A. Nadzhafova, Ozge Seşenoğlu
May 1, 2002
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Journal
Turkish Journal of Chemistry
Abstract
Pyrrole derivatives of amines and amino acids are important starting materials for the synthesis of many different biologically active compounds. A stereoselective synthesis of indolizidine alkaloids, based on the reduction of bicyclic pyrroles, has been reported . Paal-Knorr synthesis starting from primary amines and 1,4dicarbonyl compounds and their masked equivalents, such as tetrahydro-2,5-dimethoxyfuran, is often used for the construction of pyrrole rings. It was previously reported that an interaction of 2,3-dichloropropylalkyl ketones with primary amines and their functionally substituted derivatives leads to N-substituted derivatives of pyrroles3−5, while a reaction of 3-chloropropenylalkyl ketones with hydrazine hydrate leads to 1-amino-2alkylpyrroles and that of alkyl(trans-2-methoxycyclopropyl) ketones, products of 1,3-dehydrochlorination of 2-methoxy-3-chloropropylalkyl ketones, with primary amines, leads to N-substituted 2-alkylpyrroles. It was also established that different substituted pyrrole rings can be constructed from amines, amino alcohols and amino acids with various chloroenones in basic medium. In this paper, we describe the condensation reaction of 2,3-dichloropropylalkyl ketones 1a-b and 2-methoxy-3-chloropropylalkyl ketones 2a-b with alkyl 2-aminoacetate salts, which allows the synthesis of 1-alkoxycarbonylmethyl-2-alkylpyrroles 3b and 4a (80-81%) (Figure 1) in water-benzene medium at 20-25◦C followed by reflux for 6 hours.