Zeolite-Mediated Three- and Pseudo-Five-Component Reactions Involving α-Ketoglutaric Acid, Aromatic Aldehydes and 5-Aminotetrazole
- 1Department of Organic and Bioorganic Chemistry, Institute of Functional Materials Chemistry, State Scientific Institution «Institute for Single Crystals» of National Academy of Sciences of Ukraine, Nauky Ave., 60, Kharkiv, Ukraine, 61072
- 2Department of Organic Chemistry and Molecular Materials, V. N. Karazin Kharkiv National University, Svobody sq., 4, Kharkiv, Ukraine, 61022
- 3Department of Organoelement Chemistry, Institute of Organic Chemistry NAS of Ukraine, Akademika Kukharia street, 5, Kyiv, Ukraine, 02660
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.
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BibTeX
@misc{honcharov2026zeolitemediated,
title = {{Zeolite-Mediated Three- and Pseudo-Five-Component Reactions Involving α-Ketoglutaric Acid, Aromatic Aldehydes and 5-Aminotetrazole}},
author = {Vladyslav O. Honcharov and Valentyn A. Chebanov and Olena H. Shvets and Vyacheslav E. Saraev and Svitlana V. Shishkina and Yana I. Sakhno},
howpublished = {ChemRxiv},
year = {2026},
month = sep,
doi = {10.26434/chemrxiv.15009165/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009165/v1},
note = {CC BY-NC-ND},
}
RIS
TY - UNPB
TI - Zeolite-Mediated Three- and Pseudo-Five-Component Reactions Involving α-Ketoglutaric Acid, Aromatic Aldehydes and 5-Aminotetrazole
AU - Vladyslav O. Honcharov
AU - Valentyn A. Chebanov
AU - Olena H. Shvets
AU - Vyacheslav E. Saraev
AU - Svitlana V. Shishkina
AU - Yana I. Sakhno
PY - 2026
DA - 2026/09/21
PB - ChemRxiv
DO - 10.26434/chemrxiv.15009165/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009165/v1
AB - 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.
ER -