Synthesis of Multisubstituted Indanedione Based Spiropyrans via Oxa‐Michael/Michael Cascade Reaction

Abstract

Dedicated to Prof. Kwunmin ChenA sequential formal [4 + 2] cyclization involving cascade protocol has been developed for the construction of multisubstituted six-membered spirocyclic scaffolds by using 2arylidene-1, 3-indanedione and nitro allylic alcohol. This method generates four stereocenters in spiropyran ring with high diastereoselctivity (99 : 1) under mild reaction conditions.

[3+2] regioselective annulation reaction of 2-arylidene-1,3-indandiones towards synthesis of spirocyclopentenes: understanding the mechanism of γ-attackvs.α-attack using DFT studies

“… 27 Very recently, Zheng and Er-Qing carried out a phosphine catalysed [3+2] cyclisation with γ-methyl allenoates for the synthesis of spirocyclopentene as α-adduct (eqn (b), Scheme 1 ). 28 In continuation with our interest towards the synthesis of spiro carbocycles, 29 we herein report a regioselective [3+2] cyclisation of 2-arylidene-1,3-indandiones and 2,3-butadienoate catalysed by triphenylphosphine (eqn (c), Scheme 1 ). To the best of our knowledge, this is the first report for the synthesis of functionalised spirocyclopentenes as γ-addition as well as α-addition adduct.…”

Recent advances in the synthetic applications of Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes

“…In 2021, Anwar et al extended the reaction of 2-arylidene-1,3-indanediones 16 with secondary MBH alcohols 25 to afford spiro compounds 100 (Scheme 37). 49 The reaction was cata-…”

“…In 2021, Anwar et al extended the reaction of 2-arylidene-1,3-indanediones 16 with secondary MBH alcohols 25 to afford spiro compounds 100 (Scheme 37). 49 The reaction was catalyzed by potassium carbonate, and the highly substituted spiropyrans 100 were obtained in good yields and excellent diastereomeric ratios. They also carried out a one-pot synthesis of spiropyrans by synthesizing 2-arylidene-1,3-indanediones 16 in situ followed by reacting them with MBH alcohols 25 .…”

N-Benzyloxyacrylamides as Bisnucleophiles in an Organocatalyzed Domino aza-Michael/Morita-Baylis-Hillman Sequence

“…These two first elaborations emphasize the interesting ambivalent nature of the exocyclic alkene bond carried by the domino products. Going one step further, a domino oxa-Michael/Michael was next studied by reaction with 1,3-indanedione derivative 10 employing conditions described in the literature for allylic alcohols . Rewardingly, the targeted original tetracyclic spiro-product 6b bearing four stereogenic centers was isolated in 60% yield with a 68:32 dr.…”