The Preparation of Various New Heterocyclic Compounds via Cyclization of Substituted Derivatives of Phenacyl Esters of Hydrazonoacetic Acid

Melnicky, Radek; Grepl, Martin; Lyčka, Antonı́n; Bertolasi, Valerio; Kvapil, Lubomír; Dvořáková, Barbora; Hradil, Pavel

doi:10.1055/s-0033-1339348

Synthesis

2013

DOI: 10.1055/s-0033-1339348

|View full text |Cite

The Preparation of Various New Heterocyclic Compounds via Cyclization of Substituted Derivatives of Phenacyl Esters of Hydrazonoacetic Acid

Radek Melnicky

Martin Grepl

Antonı́n Lyčka

et al.

Abstract: A procedure for the preparation of derivatives of phen- acyl hydrazonopropanoates and their application in the synthesis of various heterocycles has been developed. Not only is the preparation of indole derivatives described, but also a new method for the preparation of previously unknown pyridazine derivatives

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2014

2019

Publication Types

Select...

Article5

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 7 publications

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Umpolung Reactivity of Aldehydes toward Carbon Dioxide

Juhl

Lee

2018

Angewandte Chemie

View full text Add to dashboard Cite

Carbon dioxide is an intrinsically stable molecule. Therefore,its activation requires extra energy input in the form of reactive reagents and/or activated catalysts and, often, harsh reaction conditions.R eported here is ad irect carboxylation reaction of aromatic aldehydes with carbon dioxide to afford a-keto acids as added-value products.I ns itu generation of ar eactive cyanohydrin was the key to the successful carboxylation reaction under operationally mild reaction conditions (25-40 8 8C, 1atm CO 2 ). The resulting a-keto acids served as ap latform for a-amino acid synthesis by reductive amination reactions,i llustrating the chemical synthesis of essential bioactive molecules from carbon dioxide. Scheme 1. Carboxylation reactions with CO 2 in:1)the Calvin-Benson-Bassham cycle (top), and 2) using the aldehyde-umpolung approach (bottom).Scheme 2. Potential carboxylation reaction using the Breslow intermediate.

show abstract

Umpolung Reactivity of Aldehydes toward Carbon Dioxide

Juhl

Lee

2018

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Umpolung Reactivity of Aldehydes toward Carbon Dioxide

Juhl

Lee

2018

Angew Chem Int Ed

View full text Add to dashboard Cite

Carbon dioxide is an intrinsically stable molecule. Therefore, its activation requires extra energy input in the form of reactive reagents and/or activated catalysts and, often, harsh reaction conditions. Reported here is a direct carboxylation reaction of aromatic aldehydes with carbon dioxide to afford α-keto acids as added-value products. In situ generation of a reactive cyanohydrin was the key to the successful carboxylation reaction under operationally mild reaction conditions (25-40 °C, 1 atm CO ). The resulting α-keto acids served as a platform for α-amino acid synthesis by reductive amination reactions, illustrating the chemical synthesis of essential bioactive molecules from carbon dioxide.

show abstract

Efficient Synthesis of Mandel Acetates by Electrochemical Carboxylation of Benzal Diacetates

et al. 2019

View full text Add to dashboard Cite

Efficient synthesis of mandel acetate, 2‐acetoxy‐2‐phenylacetic acid, from benzaldehyde was successfully performed in two steps using electrochemical carboxylation of benzal diacetate as a key step. When benzal diacetate, readily prepared from benzaldehyde and acetic anhydride in one step, in DMF containing 0.1 M Bu4NBF4 was electrolyzed in the presence of carbon dioxide using an undivided cell equipped with a platinum plate cathode and a magnesium rod anode under constant current conditions, reductive cleavage of the C‐OAc bond followed by capture of carbon dioxide took place efficiently at the benzylic position to give mandel acetate in good to high yields. Wide scope, high yields and the use of carbon dioxide as a carbon source of the carboxyl group would provide novel environmentally‐benign synthesis of mandelic acid derivatives.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

The Preparation of Various New Heterocyclic Compounds via Cyclization of Substituted Derivatives of Phenacyl Esters of Hydrazonoacetic Acid

Cited by 7 publications

References 10 publications

Umpolung Reactivity of Aldehydes toward Carbon Dioxide

Umpolung Reactivity of Aldehydes toward Carbon Dioxide

Umpolung Reactivity of Aldehydes toward Carbon Dioxide

Efficient Synthesis of Mandel Acetates by Electrochemical Carboxylation of Benzal Diacetates

Contact Info

Product

Resources

About