849-09-2Relevant academic research and scientific papers
Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with in Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds
Pramanik, Sayan,Ray, Suman,Maity, Suvendu,Ghosh, Prasanta,Mukhopadhyay, Chhanda
, p. 2240 - 2252 (2021/03/18)
An efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindol
DBU-catalyzed [3 + 2] cycloaddition and Michael addition reactions of 3-benzylidene succinimides with 3-ylidene oxindoles and chalcones
Tehri, Piyush,Peddinti, Rama Krishna
supporting information, p. 3964 - 3970 (2019/04/30)
A metal-free DBU catalyzed protocol has been developed for the regioselective [3 + 2] cycloaddition reactions of 3-benzylidene succinimides with 3-ylidene oxindoles to furnish spirooxindole derivatives. The 3-benzylidene succinimides underwent Michael addition with chalcones to provide benzylidene succinimide-tethered propanones. All the reactions proceeded under mild conditions and the products were isolated by simple filtration and washing with ethanol in good yields. The current methodology utilizes simple precursors and provides functionally-rich succinimides with two to five contiguous stereocenters in excellent diastereoselectivity and with complete regioselectivity.
Isocyanide-based multicomponent reactions: Concise synthesis of spirocyclic oxindoles with molecular complexity by using a [1,5]-hydrogen shift as the key step
Su, Shikuan,Li, Chunju,Jia, Xueshun,Li, Jian
, p. 5905 - 5909 (2014/05/20)
A concise multicomponent reaction of isocyanide, α-substituted allenoate, and methyleneindolinone has been disclosed. This protocol provides a fast and straightforward approach to synthesize unusual tricyclic oxindoles in an efficient and atom-economic manner. Mechanistically, the present cycloaddition may proceed through a cascade sequence involving double Michael addition, double cyclization, double [1,5]-hydrogen shift, and group migration. The introduction of a special alkyl group to the allenoate is believed to play a key role in the cascade reaction. This method also features a broad substrate scope, which is particularly useful for the delivery of a large number of compounds. Shift your perspective! An unprecedented cascade reaction, under mild conditions, involving a double Michael addition, double cyclization, and double [1,5]-hydrogen shift, followed by group migration is disclosed. This reaction offers a fast and straightforward approach to unusual polycyclic spirooxindoles (see scheme).
