Advances in Solid-Phase Cycloadditions for Heterocyclic Synthesis

Feliu, Lidia; Vera‐Luque, Patricia; Alberício, Fernando; Álvarez, Mercedes

doi:10.1021/cc070019z

Cited by 37 publications

(9 citation statements)

References 127 publications

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“…3 1,3-Dipolar cycloadditions (Figure 1) are among the most important and versatile synthetic methods for the preparation of five membered heterocycles. 4 This cycloaddition proceeds by a concerted mechanism of the [3 þ 2] type, and the interaction between asymmetric reagents can form two isomers depending on the relative position of the substituent.…”

Section: Introductionmentioning

confidence: 99%

Orbital Signatures as a Descriptor of Regioselectivity and Chemical Reactivity: The Role of the Frontier Orbitals on 1,3-Dipolar Cycloadditions

et al. 2011

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The FERMO concept emerges as a powerful and innovative implement to investigate the role of molecular orbitals applied to the description of breakage and formation of chemical bonds. In this work, Hartree-Fock (HF) theory and density functional (DFT) calculations were performed for a series of four reactions of 1,3-dipolar cycloadditions and were analyzed by molecular orbital (MO) energies, charge transfer, and molecular dynamics (ADMP) techniques for direct dynamics using the DFT method. The regioselectivity for a series of four 1,3-dipolar cycloaddition reactions was studied here using global and local reactivity indexes. We observed that the HOMO energies are insufficient to describe the behavior of these reactions when there is the presence of heteroatoms. By using the frontier effective-for-reaction molecular orbital (FERMO) concept, the reactions that are driven by HOMO, and those that are not, can be better explained, independent of the calculation method used, because both HF and Kohn-Sham methodologies lead to the same FERMO.

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Section: Introductionmentioning

confidence: 99%

Orbital Signatures as a Descriptor of Regioselectivity and Chemical Reactivity: The Role of the Frontier Orbitals on 1,3-Dipolar Cycloadditions

et al. 2011

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“…262,263 Scheme 77 Diastereoselective 1,3-dipolar cycloaddition reactions are of particular interest for the synthesis of heterocyclic compounds. 210, 264 ± 268 Diastereoselective synthesis of pyrazolines 185 is exemplified by the reaction between bis(trityl)nitrile imine (186) and (R)-a-(acryloxy)-b,b-dimethylg-butyrolactone 187 (Scheme 78).…”

Section: Scheme 76mentioning

confidence: 99%

Hydrazones as substrates for cycloaddition reactions

Belskaya¹,

Eliseeva²,

Бакулев³

2015

Russ. Chem. Rev.

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“…In recent years, design and synthesis of pharmacologically relevant heterocyclic molecules by combinatorial techniques have proven to be a promising strategy in the search for new pharmaceutical lead structures. , For these reasons, combinatorial chemistry has emerged as a powerful methodology for the preparation of libraries of small organic compounds to accelerate the drug discovery process. , Substituted heterocyclic compounds offer a high degree of structural diversity and have proven to be broadly useful as therapeutic agents. As a result, an increasing range and number of pharmaceutically useful heterocyclic compounds have been prepared using the solid-phase strategy. − This approach permits the rapid synthesis of large numbers of individual compounds as well as mixture-based combinatorial libraries in a short time frame and facilitates their use in high-throughput screening . The design and synthesis of novel scaffolds as core structures for the library generation of small molecules on solid-phase are essential steps in accessing a wide variety of structurally complex derivatives.…”

Section: Introductionmentioning

confidence: 99%