Regioselective four-component synthesis of new tetrazolo[1,5-a]quinoline-based 2-amino-1,4-dihydropyridine and pyridin-2(1H)-one derivatives using nano-ZnO catalysis
- 87 Downloads
Four-component reaction between primary amines, dialkylacetylendicarboxylates, tetrazolo[1,5-a] quinoline-4-carbaldehyde and ethyl-2-cyanoacetate in the presence of 1,4-diaza-bicyclo[2.2.2]octane and zinc oxide nanoparticles results to the regioselective production of new tetrazolo[1,5-a]quinoline-based 2-amino-1,4-dihydropyridine or pyridin-2(1H)-one derivatives in good to high yields. The selectivity of the catalyzed reaction toward the generation of the dihydropyridine or pyridin-2(1H)-one derivatives was found to be strongly dependent on the size of the alkyl groups in the ester moieties of the acetylenic esters. According to single-crystal X-ray diffraction and NMR studies, the pyridin-2(1H)-one derivatives involve a restricted rotation around the C–C bond connecting the tetrazoloquinoline and dihydropyridinone cyclic systems.
KeywordsTetrazolo[15-a]quinoline-4-carbaldehyde Dialkylacetylendicarboxylate Ethyl-2-cyanoacetate Zinc oxide nanoparticles Enaminone Atropisomer MCRs
The authors would like to express their appreciation for contributions of Professor Alireza Abbasi, Dr. Abolfazl Bezaatpour and Professor Nader Noroozi Pesyan to this work. Financial support of this research by University of Mohaghegh Ardabili, Iran, is gratefully acknowledged.
- 3.Upadhayaya RS, Shinde PD, Sayyed AY, Kadam SA, Bawane AN, Poddar A, Plashkevych O, Földesi A, Chattopadhyaya J (2010) Synthesis and structure of azole-fused indeno[2,1-c]quinolines and their anti-mycobacterial properties. J Org Biomol Chem 8:5661–5673. https://doi.org/10.1039/c0ob00445f CrossRefGoogle Scholar
- 5.Sangani CB, Makawana JA, Duan YT, Yin Y, Teraiya SB, Thumar NJ, Zhu HL (2014) Design, synthesis and molecular modeling of biquinoline–pyridine hybrids as a new class of potential EGFR and HER-2 kinase inhibitors. Biorg Med Chem Lett 24:4472–4476. https://doi.org/10.1016/j.bmcl.2014.07.094 CrossRefGoogle Scholar
- 8.Mungra DC, Kathrotiya HG, Ladani NK, Patel MP, Patel RG (2012) Molecular iodine catalyzed synthesis of tetrazolo[1,5-a]quinoline based imidazoles as a new class of antimicrobial and antituberculosis agents. Chin Chem Lett 23:1367–1370. https://doi.org/10.1016/j.cclet.2012.11.007 CrossRefGoogle Scholar
- 22.Nasiri F, Bayzidi M, Zolali A (2012) Reaction between enaminones and acetylenic esters in the presence of triphenylphosphine: a convenient synthesis of alkyl 2(1-benzyl-2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-indol-3-yl)acetates. Mol Divers 6:619–623. https://doi.org/10.1007/s11030-012-9389-7 CrossRefGoogle Scholar
- 23.Zare A, Hasaninejad A, Zare ARM, Parhami A, Sharghi H, Khalafi-Nezhad A (2007) Zinc oxide as a new, highly efficient, green, and reusable catalyst for microwave-assisted Michael addition of sulfonamides to α, β-unsaturated esters in ionic liquids. Can J Chem 85:438–444. https://doi.org/10.1139/vo7-050 CrossRefGoogle Scholar
- 25.Zare A, Hasaninejad A, Khalafi-Nezhad A, Zare ARM, Parhami A, Nejabat GR (2007) A green solventless protocol for Michael addition of phthalimide and saccharin to acrylic acid esters in the presence of zinc oxide as a heterogeneous and reusable catalyst. Arkivoc 1:58–69. https://doi.org/10.3998/ark.5550190.0008.107 CrossRefGoogle Scholar
- 27.Rao GD, Kaushik M, Halve A (2012) An efficient synthesis of naphtha[1,2-e]oxazinone and 14-substituted-14H-dibenzo[a, j]xanthene derivatives promoted by zinc oxide nanoparticle under thermal and solvent-free conditions. Tetrahedron Lett 53:2741–2744. https://doi.org/10.1016/j.tetlet.2012.03.085 CrossRefGoogle Scholar
- 31.Bhattacharyya P, Pradhan K, Paul S, Das AR (2012) Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media. Tetrahedron Lett 53:4687–4691. https://doi.org/10.1016/j.tetlet.2012.06.086 CrossRefGoogle Scholar