Arylidene pyruvic acids (APAs) in the synthesis of organic compounds

Shiri, Morteza; Heravi, Majid M.; Soleymanifard, Bita

doi:10.1016/j.tet.2012.05.009

Cited by 20 publications

(9 citation statements)

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“…In view of both the peculiar structural features and the important biological roles of α-ketoamides, it is not surprising that a plethora of different methods for their efficient synthesis have been and continue to be proposed. However, no comprehensive reviews dealing with the synthesis of α-ketoamides have appeared hitherto in the literature, unlike α-ketoacids − and α-ketoesters. − …”

Section: Introductionmentioning

confidence: 99%

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

2016

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The α-ketoamide motif is widely found in many natural products and drug candidates with relevant biological activities. Furthermore, α-ketoamides are attractive candidates to synthetic chemists due to the ability of the motif to access a wide range of functional group transformations, including multiple bond-forming processes. For these reasons, a vast array of synthetic procedures for the preparation of α-ketoamides have been developed over the past decades, and the search for expeditious and efficient protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged since the 1990s up to the present. The different synthetic routes have been grouped according to the way the α-ketoamide moiety has been created. Thus, syntheses of α-ketoamides proceeding via C(2)-oxidation of amide starting compounds are detailed, as are amidation approaches installing the α-ketoamide residue through C(1)-N bond formation. Also discussed are the methodologies centered on C(1)-C(2) σ-bond construction and C(2)-R/Ar bond-forming processes. Finally, the literature regarding the synthesis of α-ketoamide compounds by palladium-catalyzed double-carbonylative amination reactions is discussed.

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Section: Introductionmentioning

confidence: 99%

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

2016

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“…Arylidene pyruvic acids (APAs) of a versatile structure have been used as starting materials for the synthesis of a large diversity of organic compounds [1]. In addition, this functionality is associated with biological properties and is present in a series of bioactive natural products [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds

Lozynskyi

Zimenkovsky

Lesyk

2015

Heterocyclic Communications

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Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compoundsAbstract: Novel rel-(5R,6S,7S)-2- oxo-5,7-diaryl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazol-6-yl-oxo-acetic acids were synthesized in 52-70% yields via regioselective and diastereoselective hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with a series of arylidene pyruvic acids. The synthesized compounds were evaluated for anticancer activity in NCI60 cancer cell lines and for antiexudative activity on the carrageenan edema model in rats. Biological screening data led to identification of 3e as having moderate antitumor activity on the colon cancer HT-29 cell line and of 3b as having promising antiexudative effect.

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“…This Review begins by describing the methods for the preparation of various α-oxoesters, followed by the use of them to synthesize heterocycles in the arrangement of N -, O -, N , O -, N , S -, S -, and S , O -heterocycles in the ring size order of three-, four-, five-, six-, and seven-membered heterocycles. However, there are some review articles about special derivatives of α-oxoesters or similar structures, “arylidene pyruvic acids”, “( E )-2-oxo-3-butenoates”, and “benzoylpyruvates”, but to the best of our knowledge, there are no reviews and book chapters in the field of α-oxoesters in heterocycles synthesis.…”

Section: Introductionmentioning

confidence: 99%