Synthesis of heterocycles via MCRs, using a name reaction in combination with another reaction

Heravi, Majid M.; Zadsirjan, Vahideh

doi:10.1016/b978-0-12-818584-1.00003-3

Cited by 2 publications

(1 citation statement)

References 221 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Well-known examples of the transformations are represented by Ugi, Passerini, and Mannich reactions, occasionally in combination with Diels–Alder cycloadditions . However, the creation of novel one-pot sequences starting from available materials still remains a major challenge . While [4 + 2] cycloadditions are often embedded as reaction steps in MCRs, surprisingly, the Alder-ene reaction, bearing equally high synthetic potential, has remained a largely underexplored one-pot process .…”

Section: Introductionmentioning

confidence: 99%

Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids

Alekseeva,

Nadirova,

Zaytsev

et al. 2023

J. Org. Chem.

View full text Add to dashboard Cite

Diversely substituted, partially saturated benzo[f ]isoindole-4-carboxylic acids were synthesized by a new threecomponent reaction (3CR) starting from cinnamic amines (3-arylallylamines), maleimides, and maleic anhydride. The process consists of N-acylation of the amines by maleic anhydride, intramolecular [4 + 2] cycloaddition in vinylarenes (the IMDAV reaction), and the concluding Alder-ene reaction between Diels−Alder intermediates and maleimides. All of the reaction steps proceed in a highly regio-and stereoselective manner, furnishing five adjacent chiral centers and leading to a single diastereoisomer of the title compound. The efficiency of the transformation is secured by thermal conditions or utilization of soft Lewis acids (Yb(OTf) 3 ) as catalysts. The kinetics and mechanism of the 3CR were studied by using dynamic 19 F NMR. Based on the NMR data and density functional theory (DFT) calculations, the IMDAV, not the Alder-ene, reaction is the rate-limiting step of the entire process.

show abstract

Section: Introductionmentioning

confidence: 99%

Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids

Alekseeva,

Nadirova,

Zaytsev

et al. 2023

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

A Comparative Study of Microwave-Assisted and Conventional Heating Approaches for the Multicomponent Synthesis of 4,6-Diarylpyrimidines

Becerra-Rivas,

Cuervo-Prado,

Orozco-Lopez

2023

Universitas Scientiarum

View full text Add to dashboard Cite

A series of 2-amino-4,6-diarylpyrimidines were synthesized using a Biginelli-type three-component strategy optimized in conventional-heated reflux, in contrast to a non-conventional approach using a mono-mode microwave reactor. Conventional heating protocols involved organic solvents and general base catalysis, whereas a microwave-assisted method followed experimental protocols framed within the principles of green chemistry by using CaCl2 as a catalyst in solvent-free conditions. This study revealed that although conventional heating led to the main product in higher yields at longer reaction times, the microwave strategy suceeded in substantially shorter reaction times, with yields ranging from acceptable to good and efficiencies comparable to conventional heating methodology.

show abstract

Synthesis of heterocycles via MCRs, using a name reaction in combination with another reaction

Cited by 2 publications

References 221 publications

Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids

Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids

A Comparative Study of Microwave-Assisted and Conventional Heating Approaches for the Multicomponent Synthesis of 4,6-Diarylpyrimidines

Contact Info

Product

Resources

About