A concise route to fused tetrazolo scaffolds through 10-camphor sulfonic acid auto-tandem homogeneous catalysis and mechanistic investigation
- Title
- A concise route to fused tetrazolo scaffolds through 10-camphor sulfonic acid auto-tandem homogeneous catalysis and mechanistic investigation
- Creator
- Devasia J.; Nizam A.; Muthukumar D.; Pillai R.S.; Joy F.
- Description
- 10-Camphor sulfonic acid (10-CSA) as an organo-catalyst has gained interest due to its versatile solubility and easiness of handling. This work reports a simple synthetic method through non-classical Biginelli for the construction of tetrazolo pyrimidine (4a-m) and quinazolines (4a?-o?). Azolopyrimidines and quinazolines are of great pharmaceutical importance. Numerous compounds are currently in use for the treatment of different diseases. Therefore their synthesis is industrially inevitable. Employing aldehydes, 1,3-dicarbonyls, and 5-Aminotetrazole, we report eco-friendly, cost-effective catalysis through a tandem reaction catalyzed by the 10-CSA that gave excellent yields, 7095 % for tetrazolo quinazoline and 4576 % tetrazolo pyrimidines respectively. The homonuclear NOESY analysis confirms the selective formation of one isomer. All the compounds are characterised by 1H NMR, 13C NMR, and MS. Investigation of the reaction mechanism by both experimental and theoretical studies provides evidence. Mechanism of the reaction was also explained utilizing the information from mass spectrometry monitoring. DFT calculation carried out at PBEPBE (Perdew-Burke-Ernzerhof) functional and 6-31G (d,p) basis set level of theory of the various intermediates observed supports the experimental evidence. 2023 Elsevier B.V.
- Source
- Journal of Molecular Liquids, Vol-376
- Date
- 2023-01-01
- Publisher
- Elsevier B.V.
- Subject
- 10-CSA; Aminotetrazole; Auto-tandem reactions; Bronsted acid; DFT; Tetrazolo pyrimidine; Tetrazolo quinazoline
- Coverage
- Devasia J., Department of Chemistry, CHRIST (Deemed to be University), Bangalore, 560029, India; Nizam A., Department of Chemistry, CHRIST (Deemed to be University), Bangalore, 560029, India; Muthukumar D., Department of Chemistry, CHRIST (Deemed to be University), Bangalore, 560029, India; Pillai R.S., Department of Chemistry, CHRIST (Deemed to be University), Bangalore, 560029, India; Joy F., Department of Chemistry, CHRIST (Deemed to be University), Bangalore, 560029, India
- Rights
- Restricted Access
- Relation
- ISSN: 1677322; CODEN: JMLID
- Format
- Online
- Language
- English
- Type
- Article
Collection
Citation
Devasia J.; Nizam A.; Muthukumar D.; Pillai R.S.; Joy F., “A concise route to fused tetrazolo scaffolds through 10-camphor sulfonic acid auto-tandem homogeneous catalysis and mechanistic investigation,” CHRIST (Deemed To Be University) Institutional Repository, accessed February 24, 2025, https://archives.christuniversity.in/items/show/14321.