A new InCl3-catalyzed, facile and efficient method for the synthesis of spirooxindoles under conventional and solvent-free microwave conditions

Shanthi, Gnanamani; Subbulakshmi, Ganesan; Perumal, Paramasivan T.

doi:10.1016/j.tet.2006.12.042

Cited by 194 publications

(67 citation statements)

References 19 publications

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“…The spirooxindole system is the core structure of many pharmacological agents and natural alkaloids [10][11][12]. Therefore, a number of methods have been reported for the preparation of spirooxindole fused heterocycles [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Three‐component synthesis of spiro[indoline‐3,5′‐pyrimido[4,5‐b]quinoline]‐triones in water

Jadidi¹,

Ghahremanzadeh²,

Mirzaei³

et al. 2011

Journal of Heterocyclic Chem

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Section: Introductionmentioning

confidence: 99%

Three‐component synthesis of spiro[indoline‐3,5′‐pyrimido[4,5‐b]quinoline]‐triones in water

Jadidi¹,

Ghahremanzadeh²,

Mirzaei³

et al. 2011

Journal of Heterocyclic Chem

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“…[15] This three-component condensation leads to corresponding 2-amino-4H-chromene scaffold with a fused isatin fragment in 65-90% reaction yields, but necessitates either reflux in acetonitrile for 2 h or microwave irradiation and fails with aminonaphthols. Furthermore, column chromatography is required for purification of the desired products.…”

Section: Introductionmentioning

confidence: 99%

Catalysis of Salicylaldehydes and Two Different CH Acids with Electricity: First Example of an Efficient Multicomponent Approach to the Design of Functionalized Medicinally Privileged 2‐Amino‐4H‐Chromene Scaffold

et al. 2008

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Electrochemically induced multicomponent transformation of salicylaldehydes and two different C À H acids in alcohols in an undivided cell in the presence of sodium bromide as an electrolyte results in the efficient and selective formation of diversely functionalized, medicinally privileged 2-amino-4H-chromene scaffolds in 65-86% yields. The developed electrocatalytic system affords the distinction between two C À H acids according to their reactivity, and offers an efficient approach to the 2-amino-4H-chromene scaffold with a predefined arrangement of desired substituents. The electrocatalytic multicomponent reaction smoothly proceeds with salicylaldehydes bearing both electron-donating and electron-withdrawing groups. Thus, fifteen previously inaccessible, close structural analogues of the tumor antagonists HA14-1 and MX58151 have been synthesized. The electrocatalytic process was found to be advantageous in terms of selectivity and yields compared to classic chemical base catalysis, and includes a remarkable mechanistic feature that is promising for the further development of 2-amino-4H-chromene chemistry. The application of this convenient electrocatalytic multicomponent method to the formation of medicinally relevant 2-amino-4H-chromenes is also beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel, facile and environmentally benign synthetic concept for multicomponent reaction strategy.

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“…[BMIm]BF4 [18], L-proline [19], ethylenediaminediacetate [20], indium chloride (InCl3) [21], triethyle amine (NEt3) [22], electrogenerated base (NaBr/ROH) [23], cyclodextrin [24], and surfactant metal carboxylates [25] have been studied till now. Although a variety of methods and catalyst are available, some of them have disadvantages such as, harsh reaction conditions, long reaction times, and use of expensive, unsafe, and unreusable catalysts.…”

Section: Introductionmentioning

confidence: 99%

Sulfonic acid supported on Fe2O3/VO2 nanocatalyst: A highly efficient and reusable nanocatalyst for synthesis of spirooxindole derivatives

Hassani¹,

Nozarie²

2018

Asain J. Green Chem.

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A new InCl3-catalyzed, facile and efficient method for the synthesis of spirooxindoles under conventional and solvent-free microwave conditions

Cited by 194 publications

References 19 publications

Three‐component synthesis of spiro[indoline‐3,5′‐pyrimido[4,5‐b]quinoline]‐triones in water

Three‐component synthesis of spiro[indoline‐3,5′‐pyrimido[4,5‐b]quinoline]‐triones in water

Catalysis of Salicylaldehydes and Two Different CH Acids with Electricity: First Example of an Efficient Multicomponent Approach to the Design of Functionalized Medicinally Privileged 2‐Amino‐4H‐Chromene Scaffold

Sulfonic acid supported on Fe2O3/VO2 nanocatalyst: A highly efficient and reusable nanocatalyst for synthesis of spirooxindole derivatives

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