One-pot gram-scale synthesis of γ-hydroxybutenolides through catalyst-free annulation of α-amino acids with α-keto acids in water

He, Zhiqing; Fang, Fang; Lv, Jianguang; Zhang, Jianmin

doi:10.1016/j.tetlet.2017.01.080

Cited by 8 publications

(2 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2017, Zhang and co-workers reported a catalyst-free route to access γ-hydroxybutenolides 179 through the annulation reaction between aliphatic α-keto acids 1 and aryl-substituted α-amino acids 190 in aqueous medium. The reaction was performed by mixing the α-amino acid 190 and a large excess of the α-keto acid 1 (10 equiv) in the presence of H 2 O (0.5 mL/mmol).…”

Section: α-Keto Acids In Cyclization Reactionsmentioning

confidence: 99%

“…In 2017, Zhang and co-workers 299 donor and electron-withdrawing groups in the pendent phenyl ring were successfully employed, and no direct influence of electronic effects of the substituents was observed in the reaction yield of the products 179p−y. In this work, there is no mention of the use of PGA 1a or other aromatic glyoxylic acids, and only pyruvic acid 1u and 2-oxobutyric acid 1v were used as an acyl source.…”

Section: Chemical Reviewsmentioning

confidence: 99%

See 1 more Smart Citation

α-Keto Acids: Acylating Agents in Organic Synthesis

et al. 2019

View full text Add to dashboard Cite

A significant number of important acyl-transfer reactions, such as direct acylation, ortho acylation, heteroatom acylation, and a diversity of cyclization reactions using the title compound as a key starting material, have been described in recent years. Just like a sleeping beauty, α-oxocarboxylic acids were awakened from a 17-year sleep to become important reagents in classical and new acylation reactions. The greener characteristic of the coproduct formed in reactions using α-keto acid (only CO 2 ), together with its versatility as a building block in catalytic organic synthesis, accredit it as a candidate to green acylating agent, an alternative to acyl chloride, and other acyl-transfer reagents. This review presents the impressive breakthroughs achieved mainly in the past decade in the development of new catalytic reactions for the formation of C−C, C−N, and C−S bonds using α-keto acids. CONTENTS 1. Introduction 7113 2. Classical Methods and Recent Advances in the Synthesis of α-Keto Acids 7115 2.1. Physical Properties of α-Keto Acids 7119 3. α-Keto Acids in Acylation Reactions 7119 3.1.

show abstract

Section: α-Keto Acids In Cyclization Reactionsmentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

α-Keto Acids: Acylating Agents in Organic Synthesis

et al. 2019

View full text Add to dashboard Cite

show abstract

α‐Keto Thioesters as Building Blocks for Accessing γ‐Hydroxybutenolides and Oxazoles

Mal

Das

2017

Adv Synth Catal

View full text Add to dashboard Cite

Abstractα‐Keto thioesters, with two electrophilic carbon centres, have been found to react differently with β‐keto esters and isocyanoacetates. They undergo base induced Knoevenagel‐type condensation on the keto carbonyl group with β‐keto esters, followed by intramolecular cyclization and water addition leads to highly substituted γ‐hydroxybutenolides. On the other hand, substituted oxazole derivatives have been obtained using isocyanoacetates via nucleophilic displacement on the thioester carbonyl followed by intramolecular cyclization. Further functionalization of the γ‐hydroxybutenolides is also demonstrated via a BF3.OEt2‐mediated cation‐driven nucleophilic addition of terminal alkynes to access multiply substituted butenolides.magnified image

show abstract

Water-Mediated Catalyst-Free Organic Transformations

Banerjee

2020

Nanotechnology in the Life Sciences

View full text Add to dashboard Cite

One-pot gram-scale synthesis of γ-hydroxybutenolides through catalyst-free annulation of α-amino acids with α-keto acids in water

Cited by 8 publications

References 29 publications

α-Keto Acids: Acylating Agents in Organic Synthesis

α-Keto Acids: Acylating Agents in Organic Synthesis

α‐Keto Thioesters as Building Blocks for Accessing γ‐Hydroxybutenolides and Oxazoles

Water-Mediated Catalyst-Free Organic Transformations

Contact Info

Product

Resources

About