volume 87 issue 21

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
Publication typeJournal Article
Publication date2022-10-04
scimago Q2
wos Q1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
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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GOST Copy
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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@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}
}