The Synthesis of Sulfonyl Fluoride Functionalized 2-Aminothiazoles Using a Diversity Oriented Clicking Strategy DOI

Joshua W. Kop,

Carol Hua, Daniel L. Priebbenow

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 16, 2024

We present a Diversity Oriented Clicking approach to synthesize library of novel clickable N-substituted 2-aminothiazoles which serve as versatile hubs for SuFEx click chemistry diversification. Leveraging the spring-loaded reactivity 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) connectors, transformation is simple perform, tolerant wide range functionality, and regioselective single product. Finally, we propose detailed stepwise reaction mechanism that supported by experimental computational analysis.

Language: Английский

Recent Advances in the Application of 2‐Aminobenzothiazole to the Multicomponent Synthesis of Heterocycles DOI Creative Commons
Ramin Javahershenas, Jianlin Han, Mosstafa Kazemi

et al.

ChemistryOpen, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 9, 2024

Abstract Heterocycles are a vital class of compounds in numerous fields, including drug discovery, agriculture, and materials science. Efficient methods for the synthesis heterocycles remain critical meeting demands these industries. Recent advances multicomponent reactions (MCRs) utilizing 2‐aminobenzothiazole (ABT) have shown promising results formation heterocycles. The versatility this context has enabled rapid efficient construction diverse heterocyclic structures. Various synthetic methodologies involving discussed, highlighting its importance as valuable building block complex potential applications discovery material science also explored. Overall, review provides comprehensive overview current state research field offers insights into future directions area study. We highlight ABT versatile sustainable starting via MCRs, with significant implications chemical industry.

Language: Английский

Citations

20

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis DOI Creative Commons
Brenno A. D. Neto,

Rafael O. Rocha,

Marcelo O. Rodrigues

et al.

Molecules, Journal Year: 2021, Volume and Issue: 27(1), P. 132 - 132

Published: Dec. 27, 2021

In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields shortening reaction times, is vital achieving greener protocols furthering MCR field research. Considering that MCRs typically have two or more possible pathways explain transformation, essential for selecting a route avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts reagent quantities, were analyzed. Solvent effects, which are likely most neglected topic in MCRs, well their catalysis, critically discussed. Stereocontrolled rarely observed without presence catalytic system, also presented discussed review. Perspectives on use systems improved finally presented.

Language: Английский

Citations

59

Spectroscopic and molecular electronic property investigation of 2-phenylpyrimidine-4, 6-diamine via 1H NMR, UV–vis, FT-Raman, FT-IR, and DFT approach DOI
Tomsmith O. Unimuke, Hitler Louis, Wilfred Emori

et al.

Journal of Molecular Structure, Journal Year: 2022, Volume and Issue: 1263, P. 133195 - 133195

Published: April 30, 2022

Language: Английский

Citations

41

Recent Advances in the Multicomponent Synthesis of Heterocycles Using 5-Aminotetrazole DOI
Ramin Javahershenas, Ata Makarem, Haibo Mei

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(16), P. 2445 - 2461

Published: Jan. 8, 2024

Abstract The unique reactivity and beneficial features of the 5-aminotetrazole synthon (1H-tetrazol-5-amine) have made it a versatile effective building block in synthesis heterocyclic compounds. In addition, several drugs containing this scaffold with wide array biological properties been already introduced. Heterocyclic structures are backbone many biologically active industrially important 5-Aminotetrazole is one favored synthons used preparation heterocycle-bearing compounds, especially multicomponent synthesis. This review highlights comprehensive overview emerging applications as key component frameworks through reactions, reported between 2017 July 2023. 1 Introduction 2 3 Tetrazolopyrimidine Compounds 4 Spiro 5 Miscellaneous 6 Conclusion

Language: Английский

Citations

7

Arylglyoxal-based multicomponent synthesis of C-3 functionalized imidazoheterocycles DOI
Swadhin Swaraj Acharya,

Rahul Kumar Sahoo,

Pralina Mohanty

et al.

Chemical Papers, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 10, 2024

Language: Английский

Citations

4

Ecofriendly Synthesis, Biological Evaluation, and Molecular Docking Studies of a Novel N-[3-(Benzo[d][1,3]dioxol-5-yl]-1,8-naphthyridine Benzamide Derivatives and Phenyl-triazolo-[1,8]naphthyridine Scaffolds DOI

S. Hari Krishna Reddy,

Kavati Shireesha,

Kumara Swamy Jella

et al.

Russian Journal of General Chemistry, Journal Year: 2025, Volume and Issue: 95(1), P. 173 - 183

Published: Jan. 1, 2025

Language: Английский

Citations

0

The Groebke–Blackburn–Bienaymé (GBB) Reaction: A Powerful Tool for Generating Diverse Heterocyclic Scaffold Libraries in Anticancer Drug Discovery DOI
K. L. A. Khan, Rashid Ali,

Shahnaaz Khatoon

et al.

European Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: 291, P. 117629 - 117629

Published: April 12, 2025

Language: Английский

Citations

0

Multicomponent Reactions Using C,N-Binucleophilic Nature of Aminopyrazoles: Construction of Pyrazole-Fused Heterocycles DOI
Tasneem Parvin

Topics in Current Chemistry, Journal Year: 2023, Volume and Issue: 381(4)

Published: May 26, 2023

Language: Английский

Citations

8

Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines DOI Creative Commons
Wei‐Yang Ma,

Emeric Montinho‐Inacio,

Bogdan I. Iorga

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(10), P. 1708 - 1715

Published: April 13, 2022

Abstract An enantioselective chiral phosphoric acid catalyzed formal [4+2] cycloaddition between 2‐benzothiazolimines and N ‐H‐1,3‐dienecarbamates is described. A divergence in reaction pathways was observed depending on the dienes employed. The performed with 4‐substituted produced benzothiazolopyrimidines as major product yields ranging from 42 to 67%, single diastereoisomer enantioselectivity 93 99%. same 3‐substituted dienes, however, gave highly enantioenriched 1,2,3,4‐tetrahydroquinolines products albeit moderate diastereoselectivity. magnified image

Language: Английский

Citations

13

Multi-component synthesis and enhanced photophysical study of novel azolo[1,5-a]pyrimidine based dyes DOI
Semen V. Aminov, Victor V. Fedotov, Константин В. Саватеев

et al.

Dyes and Pigments, Journal Year: 2024, Volume and Issue: 232, P. 112447 - 112447

Published: Sept. 11, 2024

Language: Английский

Citations

2