Zeolite-Mediated Three- and Pseudo-Five-Component Reactions Involving α-Ketoglutaric Acid, Aromatic Aldehydes and 5-Aminotetrazole
Year: 2026
Type: preprint
Abstract: We report previously undescribed multicomponent reactions of α-ketoglutaric acid, aromatic aldehydes, and 5-aminotetrazole that provides access to two distinct types of products. Notably, these transformations require the presence of 4A or 3A molecular sieves, and the formation of the target compounds is condition-controllable: the process can proceed through a pseudo-five-component pathway, yielding tetrahydropyrido[3,4-d]tetrazolo[1,5-a]pyrimidinone derivatives – the first examples of this heterocyclic framework – or can be directed toward a three-component condensation that affords dihydrotetrazolo[1,5-a]pyrimidine dicarboxylic acids. The latter were identified as key intermediates in the pseudo-five-component transformation, enabling the synthesis of pyrido[3,4-d]tetrazolo[1,5-a]pyrimidine systems via a two-step Doebner-type and Castagnoli–Cushman-type/decarboxylation sequence with an expanded range of possible substrates, thereby combining tetrazole, dihydropyrimidine, δ-lactam, and triazole pharmacophore motifs within a single fused framework.
Source: ChemRxiv
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7213891530