Multicomponent Synthesis of Spiro-dihydropyridine Oxindoles <i>via</i> Cascade Spiro-cyclization of Knoevenagel/Aza-Michael Adducts

Basavaraja, D; Athira, C.; Siddalingeshwar, V D; Ashitha, Kizhakkan Thiruthi; Somappa, Sasidhar B.

doi:10.1021/acs.joc.2c01063

Cited by 5 publications

(1 citation statement)

References 44 publications

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“…Therefore, many effective methods have been developed to synthesize spiro compounds . In general, isatin, due to the important reactivity of the 3-position carbonyl group, is one of the basic reagents for the construction of spiro compounds . Studies have shown that isatins generally maintain their structural integrity during this transformation (Scheme , a).…”

Section: Introductionmentioning

confidence: 99%

Construction of Spiro[benzo[a]acridine-12,4′-imidazolidine]-2′,5′-dione Derivatives via Ring-Opening and Recyclization of Isatins and C–OH Cleavage of 2-Naphthol

Rong

Liao

et al. 2023

J. Org. Chem.

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An efficient three-component reaction to access spiro[benzo[a]acridine-12,4′-imidazolidine]-2′,5′-dione derivatives has been developed through the ring-opening and recyclization process of isatins and dehydroxylation of 2-naphthol, which is different from their conventional reaction modes. Experimental observations suggest that p-toluenesulfonic acid is the key factor that promotes the success of this synthetic strategy. The research provided a novel approach for the construction of spiro compounds from isatins and 2-naphthol in organic synthesis.

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Section: Introductionmentioning

confidence: 99%

Construction of Spiro[benzo[a]acridine-12,4′-imidazolidine]-2′,5′-dione Derivatives via Ring-Opening and Recyclization of Isatins and C–OH Cleavage of 2-Naphthol

Rong

Liao

et al. 2023

J. Org. Chem.

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DBU-Catalyzed Diastereo/Regioselective Access to Highly Substituted Spiro-oxetane Oxindoles via Ring Annulation of Isatins and Allenoates

Durugappa,

C S,

Doddamani

et al. 2023

J. Org. Chem.

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A facile and efficient method for the diastereo/regioselective synthesis of highly functionalized spiro-oxetane oxindoles has been described. The 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed reaction proceeds via spiro-annulation of isatins and allenoates. The reaction is compatible with a wide range of isatins containing electron-donating groups (EDGs) and electron-withdrawing groups (EWGs) with various allenoates affording the corresponding products in acceptable yields. It is noteworthy that this is the first protocol for constructing structurally diverse motifs of highly functionalized spiro-oxetane oxindoles of pharmaceutical relevance.

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Diastereoselective Synthesis of Fused Tricyclic Pyridopyrimidines via Tandem Cyclization of Allenoates and Cyclic Amidines

Santhoshkumar,

Durugappa,

Doddamani

et al. 2023

Org. Lett.

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The tandem cyclization of easily accessible allenoates and cyclic amidines for the synthesis of functionalized tricyclic pyridopyrimidines is reported herein. The annulation featured a broad substrate scope with good functional group tolerance under very mild conditions (35 examples, 32–85% yields). The pyridopyrimidines were obtained in a very short reaction time (1 min), at room temperature, under neat conditions, which offers an alternative way to the sustainable synthesis of functionalized pyridopyrimidines. The scalability of the developed protocol is further demonstrated by a gram-scale synthesis.

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Multicomponent Synthesis of Spiro-dihydropyridine Oxindoles via Cascade Spiro-cyclization of Knoevenagel/Aza-Michael Adducts

Cited by 5 publications

References 44 publications

Construction of Spiro[benzo[a]acridine-12,4′-imidazolidine]-2′,5′-dione Derivatives via Ring-Opening and Recyclization of Isatins and C–OH Cleavage of 2-Naphthol

Construction of Spiro[benzo[a]acridine-12,4′-imidazolidine]-2′,5′-dione Derivatives via Ring-Opening and Recyclization of Isatins and C–OH Cleavage of 2-Naphthol

DBU-Catalyzed Diastereo/Regioselective Access to Highly Substituted Spiro-oxetane Oxindoles via Ring Annulation of Isatins and Allenoates

Diastereoselective Synthesis of Fused Tricyclic Pyridopyrimidines via Tandem Cyclization of Allenoates and Cyclic Amidines

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