PYRAN-2-ONE DERIVATIVES (Part 2): POWERFUL BUILDING BLOCKS AND SCAFFOLDS FOR THE CONSTRUCTION OF A WIDE RANGE OF SEVERAL HETEROCYCLIC COMPOUNDS
| Autor: | Jilalat, Alae Eddine, Chakib, Imane, El Ghayati, Lhoussaine, EL Otmani, Bouchaib, Sebbar, Nada Kheira, Essassi, El Mokhtar |
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| Jazyk: | angličtina |
| Rok vydání: | 2022 |
| Předmět: | |
| DOI: | 10.48369/imist.prsm/jmch-v21i03.36067 |
| Popis: | Pyran-2-one derivatives namely 3-acetyl-4-hydroxy-6-methyl-pyran-2-one (Dehydracetic acid: DHA) and 4-hydroxy-6-methyl-pyran-2-one (triacetic acid lactone: TAL) are widely used as a precursor in organic synthesis of various natural and synthetic products and a platform chemical for the production of commercially valuable functional chemical intermediates. Pyran-2-one compounds serve both as powerful building blocks and scaffolds for the development of novel heterocyclic compounds. This review is principally devoted to the mechanisms underlying the formation of a variety of heterocyclic systems from pyran-2- one derivatives with potent physicochemical, pharmacological and biological properties. Pyran-2-one derivatives (DHA and TAL) reactivity studies show that these heterocyclic compounds possess as electrophilic sites the acetyl group; the carbon atoms in positions 2,4,6 and as nucleophilic center the carbon atom at 5-position. We present the reactions leading to the substituted heterocyclic systems allowing to keep the pyran nucleus fused or linked to diverse five membered rings such as pyrrole, furan, thiophene, pyrazole, isoxazole, thiazole, 1,3-dioxolane, imidazole, benzimidazole, to six membered rings such as pyran, thiopyran, pyridine, pyridazine, 1,3-oxazine, quinoline, quinoxaline, quinazoline, 1,4-benzothiazine or to seven membred rings like 1,4-diazepine, 1,4-thiazepine, 1,5-benzodiazepine, 1,5-benzothiazepine or pyridotriazepine. In other reactions, pyran-2-one compounds undergo interesting rearrangement reactions involving the opening of the pyran nucleus under the effect of diverse nucleophilic reagents such as ammoniac, substituted amines, hydrazines, hydroxylamine hydrochloride, 2-amino-pyridine, 2-amino-thiazole, 5-aminopyrazole, 3-amino-1,2,4-triazole, 2-amino-benzimidazole, o-aminothiophenol, o-phenylenediamine derivatives giving rise to heterocyclic systems containing pyrazole, isoxazole, pyridone, pyrimidine, 1,5-benzodiazepine, 1,5-benzothiazepine, pyrazolopyrimidine, triazolopyrimidine, benzimidazole, 1,4-benzothiazine, pyridopyrimidine, pyrazolopyridine, 1,2,4-triazolothiazine, pyrimidobenzimidazole moieties and other heterocyclic compounds. Moroccan Journal of Heterocyclic Chemistry, Vol 21, No 03 (2022) |
| Databáze: | OpenAIRE |
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