Multicomponent Synthesis of Spiro-dihydropyridine Oxindoles via Cascade Spiro-cyclization of Knoevenagel/Aza-Michael Adducts
Basavaraja D
1, 2
,
Athira C S
1, 2
,
Siddalingeshwar V D
1, 2
,
Ashitha K T
1, 2
,
Balappa S. Sasidhar
1, 2
2
Academy of Scientific and Innovative Research (AcSIR, Ghaziabad 201002, India
|
Publication type: Journal Article
Publication date: 2022-10-04
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
36194438
Organic Chemistry
Abstract
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, Et3N-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.
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12
Total citations:
12
Citations from 2024:
7
(58.33%)
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D B. et al. Multicomponent Synthesis of Spiro-dihydropyridine Oxindoles via Cascade Spiro-cyclization of Knoevenagel/Aza-Michael Adducts // Journal of Organic Chemistry. 2022. Vol. 87. No. 21.
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D B., C S A., D S. V., T A. K., Sasidhar B. S. Multicomponent Synthesis of Spiro-dihydropyridine Oxindoles via Cascade Spiro-cyclization of Knoevenagel/Aza-Michael Adducts // Journal of Organic Chemistry. 2022. Vol. 87. No. 21.
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TY - JOUR
DO - 10.1021/acs.joc.2c01063
UR - https://doi.org/10.1021/acs.joc.2c01063
TI - Multicomponent Synthesis of Spiro-dihydropyridine Oxindoles via Cascade Spiro-cyclization of Knoevenagel/Aza-Michael Adducts
T2 - Journal of Organic Chemistry
AU - D, Basavaraja
AU - C S, Athira
AU - D, Siddalingeshwar V
AU - T, Ashitha K
AU - Sasidhar, Balappa S.
PY - 2022
DA - 2022/10/04
PB - American Chemical Society (ACS)
IS - 21
VL - 87
PMID - 36194438
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2022_D,
author = {Basavaraja D and Athira C S and Siddalingeshwar V D and Ashitha K T and Balappa S. Sasidhar},
title = {Multicomponent Synthesis of Spiro-dihydropyridine Oxindoles via Cascade Spiro-cyclization of Knoevenagel/Aza-Michael Adducts},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.joc.2c01063},
number = {21},
doi = {10.1021/acs.joc.2c01063}
}