Royal Society of Chemistry (RSC)
Organic and Biomolecular Chemistry
,  volume 23 ,  issue 11 ,  pages 2712-2720

Diastereoselective assembly of dispiro-cyclopentene-linked bisoxindoles via annulation involving isatylidene malononitriles and benzylamines

Publication type: Journal Article
Publication date: 2025-02-11
Royal Society of Chemistry (RSC)
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
Abstract
A cascade reaction utilizing benzylamines and two equivalents of isatylidene malononitriles in alcohols effectively produces dispiro[indoline-cyclopentapyrimidine-indoline] structures with high chemical yields, reaching up to 93%, and remarkable diastereoselectivity (dr ≥ 19 : 1). This one-pot synthesis, facilitated by nucleophilic solvent participation, provides a practical method for obtaining multicyclic dispiro-cyclopentene-linked bisoxindoles, generating four chiral centers in a diastereoselective fashion. The practical applicability of this approach was further illustrated through a gram-scale experiment, and the final product's structure was confirmed via single-crystal X-ray analysis, affirming the successful synthesis of the target compounds.
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Yavari I. et al. Diastereoselective assembly of dispiro-cyclopentene-linked bisoxindoles via annulation involving isatylidene malononitriles and benzylamines // Organic and Biomolecular Chemistry. 2025. Vol. 23. No. 11. pp. 2712-2720.
GOST all authors (up to 50) Copy
Yavari I., Ahmadi M., Ravaghi P., Mohsenzadeh R. Diastereoselective assembly of dispiro-cyclopentene-linked bisoxindoles via annulation involving isatylidene malononitriles and benzylamines // Organic and Biomolecular Chemistry. 2025. Vol. 23. No. 11. pp. 2712-2720.
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TY - JOUR
DO - 10.1039/d4ob01811g
UR - https://xlink.rsc.org/?DOI=D4OB01811G
TI - Diastereoselective assembly of dispiro-cyclopentene-linked bisoxindoles via annulation involving isatylidene malononitriles and benzylamines
T2 - Organic and Biomolecular Chemistry
AU - Yavari, Issa
AU - Ahmadi, Mahmoud
AU - Ravaghi, Parisa
AU - Mohsenzadeh, Ramin
PY - 2025
DA - 2025/02/11
PB - Royal Society of Chemistry (RSC)
SP - 2712-2720
IS - 11
VL - 23
SN - 1477-0520
SN - 1477-0539
ER -
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BibTex (up to 50 authors) Copy
@article{2025_Yavari,
author = {Issa Yavari and Mahmoud Ahmadi and Parisa Ravaghi and Ramin Mohsenzadeh},
title = {Diastereoselective assembly of dispiro-cyclopentene-linked bisoxindoles via annulation involving isatylidene malononitriles and benzylamines},
journal = {Organic and Biomolecular Chemistry},
year = {2025},
volume = {23},
publisher = {Royal Society of Chemistry (RSC)},
month = {feb},
url = {https://xlink.rsc.org/?DOI=D4OB01811G},
number = {11},
pages = {2712--2720},
doi = {10.1039/d4ob01811g}
}
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Yavari, Issa, et al. “Diastereoselective assembly of dispiro-cyclopentene-linked bisoxindoles via annulation involving isatylidene malononitriles and benzylamines.” Organic and Biomolecular Chemistry, vol. 23, no. 11, Feb. 2025, pp. 2712-2720. https://xlink.rsc.org/?DOI=D4OB01811G.