Multicomponent Synthesis of Spiro-dihydropyridine Oxindoles via Cascade Spiro-cyclization of Knoevenagel/Aza-Michael Adducts.

Autor: D B; Chemical Sciences & Technology Division, CSIR-National Institute for Interdisciplinary Science & Technology (NIIST), Thiruvanthapuram 695019, Kerala, India.; Academy of Scientific and Innovative Research (AcSIR, Ghaziabad 201002, India., C S A; Chemical Sciences & Technology Division, CSIR-National Institute for Interdisciplinary Science & Technology (NIIST), Thiruvanthapuram 695019, Kerala, India.; Academy of Scientific and Innovative Research (AcSIR, Ghaziabad 201002, India., D SV; Chemical Sciences & Technology Division, CSIR-National Institute for Interdisciplinary Science & Technology (NIIST), Thiruvanthapuram 695019, Kerala, India.; Academy of Scientific and Innovative Research (AcSIR, Ghaziabad 201002, India., T AK; Chemical Sciences & Technology Division, CSIR-National Institute for Interdisciplinary Science & Technology (NIIST), Thiruvanthapuram 695019, Kerala, India.; Academy of Scientific and Innovative Research (AcSIR, Ghaziabad 201002, India., Somappa SB; Chemical Sciences & Technology Division, CSIR-National Institute for Interdisciplinary Science & Technology (NIIST), Thiruvanthapuram 695019, Kerala, India.; Academy of Scientific and Innovative Research (AcSIR, Ghaziabad 201002, India.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2022 Nov 04; Vol. 87 (21), pp. 13556-13563. Date of Electronic Publication: 2022 Oct 04.
DOI: 10.1021/acs.joc.2c01063
Abstrakt: An efficient, straightforward, and one-pot synthesis of biologically relevant spiro-dihydropyridine oxindoles was described via readily available isatin, malononitrile, allenoate, and amines. The metal/organocatalyst-free, Et 3 N-mediated reaction proceeds via cascade spiro-cyclization of in situ generated Knoevenagel/aza-Michael adducts. The reaction has great flexibility over electron-rich and electron-poor substituents affording desired products in good to excellent yields. We have also demonstrated the selected spiro-dihydropyridines for late-stage diversification into new spiro-dihydropyridine hybrids of pharmaceutical relevance.
Databáze: MEDLINE