Synthesis of 2-aminopyrrole-3-carboxylates via zinc perchlorate mediated annulation of alpha-cyano-gamma-ketoesters with amines

Akca, Nazmiye Bihter
2-Aminopyrrole-3-carboxylate derivatives are important starting materials for biologically active compounds like pyrrolotriazole, pyrrolotriazine so their synthese has great importance in the synthetic organic chemistry. There are only two methods for the synthesis of 2-aminopyrrole-3-carboxylates in the literature. Therefore, there is a great need for the design and development of a new method for the synthesis of 2-aminopyrrole-3-carboxylates. In this work, 2-aminopyrrole-3-carboxylate derivatives were synthesized starting from cyano acetic acid ethyl ester with a new method. In the first step, cyanoacetic acid ethyl ester was alkylated with bromo acetone in the presence of NaH. Then, obtained gamma-ketoester was reacted with primary amines in the presence of catalytic amount of zincpechlorate (Zn(ClO4)2). As a result, 2-aminopyrrole-3-carboxylate derivatives were obtained. Cyanoacetic acid ethyl ester was also alkylated with various bromo acetophenone derivatives in the presence of DBU (1,8-Diazabicycloundec-7-ene). As a result of these reactions, different gamma-ketoesters were obtained. The reaction of these gamma-ketoesters with primary amines in the presence of catalytic amount of Zn(ClO4)2 concluded with 2-aminopyrrole-3-carboxylate derivatives.


Synthesis of Functionalized Novel alpha-Amino-beta-alkoxyphosphonates through Regioselective Ring Opening of Aziridine-2-phosphonates
Polat-Cakir, Sidika; Beksultanova, Nurzhan; Doğan, Özdemir (Wiley, 2019-11-01)
Aziridines are highly useful compounds as building blocks for the synthesis of important organic compounds. Amino acid synthesis by aziridine ring opening reaction is a good example to the use of aziridines. Although this reaction is studied by many groups, the synthesis of amino phosphonic acids is less explored. In this study, we have carried out the ring opening reaction of aziridinyl phosphonates with a variety of alcohols including the more functional propargylic and allylic alcohols. These reactions p...
Synthesis of ferrocenyl substituted pyrazoles by sonogashira and suzuki-miyaura cross-coupling reactions
Karabıyıkoğlu, Sedef; Zora, Metin; Department of Chemistry (2010)
Pyrazoles constitute one of the most important classes of heterocyclic compounds due to their interesting chemical and biochemical features. Researchers have studied many pyrazole containing structures for almost over a century in order to investigate the various biological activities possessed by these molecules. A new and important trend in these studies is to produce ferrocenyl substituted pyrazoles since ferrocene attracts considerable interest in the research field of organometallic and bioorganometall...
Synthesis of New Squaramide Based Organocatalyst and Its Application for Enantioselective Synthesis of Organic Compounds
Özdemir, Özge; Doğan, Özdemir; Department of Chemistry (2022-9-19)
Organocatalytic asymmetric synthesis of organic compounds is one of the important fields of synthetic organic chemistry. Organocatalysts are small chiral organic molecules having certain functional groups, such as hydroxy, amino, amido etc. These catalysts are environmentally more friendly than the alternative chiral metal catalysts. Therefore, they are more popular and studied more than the metal catalysts. On the other hand, there are no organocatalysts that work well for every organic reaction. Here in t...
Synthesis of 2,3-disubstituted thiophenes from ketoalkynes
Vatansever, Erol Can; Balcı, Metin; Department of Chemistry (2013)
Synthesis of thiophene containing compounds are of particular interest in synthetic organic chemistry. Besides the importance for synthetic organic chemistry, thiophene derivatives are used in applied research such as drug synthesis and study of functional materials. In this thesis, a new methodology for developing of 2,3-disubstituted thiophenes was developed. This methodology utilizes readily available compounds in a two-step synthesis to provide a facile access to the 2,3-disubstituted thiophenes. In the...
Synthesis of chiral aziridinyl phosphonates, their biological activities and organocatalytic effect of their phosphonic acid derivatives
Beksultanova, Nurzhan; Doğan, Özdemir; Department of Chemistry (2017)
Aziridines are important three-membered heterocyclic ring systems in synthetic organic chemistry and medicinal chemistry. They can be used as the building blocks for the synthesis of amino acids, amino alcohols, pyrrolidines, pyrroles, lactams, and oxazoles. Aziridinyl phosphonates are attracting more attention in recent years. They are the precursors of α-amino phosphonates that find applications such as enzyme inhibitors and antibacterial agents. One of the methods for the synthesis of these compounds is ...
Citation Formats
N. B. Akca, “Synthesis of 2-aminopyrrole-3-carboxylates via zinc perchlorate mediated annulation of alpha-cyano-gamma-ketoesters with amines,” M.S. - Master of Science, Middle East Technical University, 2008.