2021
DOI: 10.1002/slct.202004619
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Knoevenagel‐Friedel‐Crafts‐Hemiketalization Triple Cascade Reaction: A Diastereoselective Formal [1+2+3] Cyclization Towards Indenonaphthopyran Scaffolds

Abstract: A simple and efficient cascade reactionviaformal [1+2+3] cyclization of 1,3‐indanedione, aldehyde and 2‐naphthol is reported using K2CO3as a base. The advantage includes metal‐free conditions, varied substrate scope and shortened reaction duration with high diastereoselectivity (i. e., 99 : 1) resulting in the formation of two carbon‐carbon as well as two carbon‐oxygen bonds through Knoevenagel‐Friedel‐Crafts‐Hemiketalization sequence resulting in three contiguous stereocenters.

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Cited by 11 publications
(3 citation statements)
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“…In recent years, multi-component reactions containing 1,3-indanedione have been successfully developed to synthesize spiro heterocycles, spirocycles, and fused heterocycles. 57–60 The fused heterocycles are containing the 1,3-indanedione structure from important medicinal and biological frameworks. These compounds have attracted the attention of pharmacologists and chemists due to their broad scope of biological activities.…”
Section: Introductionmentioning
confidence: 99%
“…In recent years, multi-component reactions containing 1,3-indanedione have been successfully developed to synthesize spiro heterocycles, spirocycles, and fused heterocycles. 57–60 The fused heterocycles are containing the 1,3-indanedione structure from important medicinal and biological frameworks. These compounds have attracted the attention of pharmacologists and chemists due to their broad scope of biological activities.…”
Section: Introductionmentioning
confidence: 99%
“…[8] In continuation of our research interest towards spiropyrans using primary nitro allylic alcohol 5 (Eqn. b, Scheme 1) [9] and fused heterocyclic skeletons, [10] we envisioned that the synthesis of multisubstituted spirocyclic pyrans having four stereocenters via Oxa-Michael/Michael [11][12][13] through formal [4 + 2] cycloaddition cyclization reaction can be accomplished using ambiphilic substrates (1 C, 2 C) 2-arylidene-1,3-indanedione [14] 4 and (1 C, 4O) secondary nitroallylic alcohol 2. (Scheme 2).…”
Section: Introductionmentioning
confidence: 99%
“…On the other hand, the utility of nitro-styrene-derived MBH alcohols as 1,4- bis -ambiphiles (α-C, δ-O) has been less extensively investigated. 20 In continuation of our efforts towards the synthesis of various spirocyclic systems, 21 herein we report the synthesis of spiropyrazolone tetrahydropyran scaffolds using β-nitro-styrene-derived MBH alcohols, resulting in the formation of the desired products with 4 to 5 contiguous chiral centers through [4 + 2] annulation (eqn (d), Scheme 1).…”
mentioning
confidence: 99%