Catalytic asymmetric synthesis of spirooxindoles: recent developments

Arylglyoxals in synthesis of heterocyclic compounds.

Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications. This review focuses on the various strategies for the enantioselective synthesis of spirocyclic oxindoles relying on reports over the past decade and from earlier work. The spirooxindoles in this review are separated into three structural classes, and then further categorized into the method type from which the spirocycle is generated.

Molecular diversity of spirooxindoles. Synthesis and biological activity

Supported molybdenum on graphene oxide/Fe3O4: An efficient, magnetically separable catalyst for one-pot construction of spiro-oxindole dihydropyridines in deep eutectic solvent under microwave irradiation

This review surveys recent progress in the chemistry of polycyclic heteroaromatic molecules with a focus on structural diversity and synthetic methodology. The article covers literature published during the period of 2016-2020, providing an update to our first review of this topic (Chem. Rev.2017, 117 (4), 3479-3716).

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds.

A general review (138 references) focused on the recent advances in the application of Meldrum’s acid reactivity for synthesis of diverse pyridine and pyrimidine derivatives, mostly small and drug-like molecules is presented.

One hundred years of Meldrum's acid: advances in the synthesis of pyridine and pyrimidine derivatives.

The reaction of 3-amino-1,2,4-triazole with arylidene derivatives of dimedone and their potential synthetic equivalents leading to the formation of 9-aryl-6,6-dimethyl-5,6,7,9-tetrahydro-1,2,4-triazolo[5,1-b]quinazolin-8(4H)ones has been studied. The direction of heterocyclization has been established, and the possible mechanisms for the formation of the pyrimidine heterocycle have been analysed.

Synthesis of 9-Aryl-6,6-dimethyl-5,6,7,9-tetrahydro-1,2,4-triazolo[5,1-b]quinazolin-8(4H)ones

Three-component condensation of 3,5-diamino-1,2,4-triazole with aromatic aldehydes and dimedone in dimethylformamide gives 2-amino-5-aryl-8,8-dimethyl-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[3,2-b]quinazolin-6-ones. The reaction of 3,5-diamino-1,2,4-triazole with dimedone in the absence of aldehyde involves dimethylformamide as one of the carbonyl components to afford 2-amino-8,8-dimethyl-6,7,8,9-tetrahydro[1,2,4]triazolo[2,3-a]quinazolin-6-one.

Synthesis of Partially Hydrogenated 1,2,4-Triazoloquinazolines by Condensation of 3,5-Diamino-1,2,4-triazole with Aromatic Aldehydes and Dimedone

The reactions of 2-aminobenzimidazole with substituted benzaldehydes and dimedone, 2-arylidene derivatives of dimedone, 9-arylhexahydro-1H-xanthene-1,8(2H)-diones and also with dimedone and DMF have been studied. The direction of formation of the pyrimidine ring has been established and discussed. An X-ray structural investigation of 2,2-dimethyl-2,3-dihydrobenzimidazo[1,2-a]quinazolin-4(1H)-one has been carried out.

Victoria V. Lipson

Papers

Molecular diversity of spirooxindoles. Synthesis and biological activity

One hundred years of Meldrum's acid: advances in the synthesis of pyridine and pyrimidine derivatives.

Synthesis of 9-Aryl-6,6-dimethyl-5,6,7,9-tetrahydro-1,2,4-triazolo[5,1-b]quinazolin-8(4H)ones

Synthesis of Partially Hydrogenated 1,2,4-Triazoloquinazolines by Condensation of 3,5-Diamino-1,2,4-triazole with Aromatic Aldehydes and Dimedone

Cyclocondensation of 2-Aminobenzimidazole with Dimedone and Its Arylidene Derivatives