A multi-component domino reaction for the direct access to polyfunctionalized indolesvia intermolecular allylic esterification and indolation

Jiang, Bo; Yi, Mian‐Shuai; Shi, Feng; Pindi, Suresh; McDowell, Patrick; Li, Guigen

doi:10.1039/c1cc15913e

Cited by 106 publications

(33 citation statements)

References 43 publications

(15 reference statements)

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“…14 As a result of our continuous effort on these domino processes, herein, we now found a new regioselective domino annulation providing an easy access to pyrazole-fused benzo[ h ]acridine derivatives. This reaction was achieved by reacting aromatic aldehydes, indazol-5-amine and 2-hydroxy-1,4-naphthoquinone under microwave irradiation (MW) in the absence of strong acids or metal catalysts/promoters (Scheme 1).…”

Section: Introductionmentioning

confidence: 90%

Regioselective Multicomponent Domino Reactions Providing Rapid and Efficient Routes to Fused Acridines

Jiang¹,

Tu²,

Li³

et al. 2014

HETEROCYCLES

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Regioselective three-component reactions of aromatic aldehydes with indazol-5-amine and 2-hydroxy-1,4-naphthoquinone in HOAc under microwave irradiation have been developed. In this one-pot reaction, a series of new pyrazole-fused benzo[h]acridine derivatives with 1,2-diketone unit were synthesized with high chemical yields. The resulting pyrazole-fused acridines were employed to further react with aldehydes and ammonium acetate to give polycyclic oxazole-fused pyrazolo[3,4-j]acridines. The present green synthesis shows several advantages including operational simplicity and fast reaction rates, which makes it a useful and attractive process of library generation for drug discovery.

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Section: Introductionmentioning

confidence: 90%

Regioselective Multicomponent Domino Reactions Providing Rapid and Efficient Routes to Fused Acridines

Jiang¹,

Tu²,

Li³

et al. 2014

HETEROCYCLES

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“…A domino three-component reaction for the synthesis of indoles and bis-indoles 93 was developed by Tu and coworkers [68]. Various aliphatic carboxylic acids 90, arylglyoxal monohydrate 91, and N-substituted enamines 92, under microwave heating, provide the desired indole derivatives 93 in the absence of any catalyst and solvent (Scheme 28).…”

Section: Synthesis Of Indolesmentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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One-pot heterocyclic synthesis is an exciting research area as it can open routes for the development of otherwise complex transformations in organic synthesis. Heterocyclic compounds show wide spectrum of applications in medicinal chemistry, chemical biology, and materials science. These heterocycles can be generated very efficiently through highly economical and viable routes using one-pot synthesis. In particular, the metal-free one-pot synthetic protocols are highly fascinating due to several advantages for the industrial production of heterocyclic frameworks. This comprehensive review is devoted to the transition metal-free one-pot synthesis of nitrogen-containing heterocycles from the period 2010-2013.

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“…Multi-component reactions of arylglyoxals and enaminocarbonyls in the presence of different nucleophiles have been recently reported for synthesis of polyfunctionalized pyrroles [23][24][25]. However, to the best of our knowledge there are only a few reports on the simple addition of enaminocarbonyl compounds to arylglyoxals [26].…”

mentioning

confidence: 96%

“…These compounds are useful starting points for the preparation of a variety of heterocyclic compounds [17] utilized for synthesis of pharmaceuticals [18] and are building blocks for amino acids [19], peptides [20] or alkaloids [21].Designing of multi-component reactions in water is another attractive area in chemistry, because water is a cheap, safe and an environmentally benign solvent [22].Multi-component reactions of arylglyoxals and enaminocarbonyls in the presence of different nucleophiles have been recently reported for synthesis of polyfunctionalized pyrroles [23][24][25]. However, to the best of our knowledge there are only a few reports on the simple addition of enaminocarbonyl compounds to arylglyoxals [26].…”

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confidence: 99%

An efficient one-pot synthesis of polyfunctionalized 2H-pyrroline derivatives by reaction of β-enaminocarbonyls, arylglyoxals and amines

2015

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Multi-component reactions (MCRs), especially threecomponent reactions, offer significant advantages over conventional linear-type syntheses, because the combination of the reaction components to generate new products in a single step is easy and economic [12,13].β-Enaminocarbonyls are important compounds used for selective alkylation and acylation of carbonyl compounds and valuable intermediates for the synthesis of biologically active compounds [14][15][16]. These compounds are useful starting points for the preparation of a variety of heterocyclic compounds [17] utilized for synthesis of pharmaceuticals [18] and are building blocks for amino acids [19], peptides [20] or alkaloids [21].Designing of multi-component reactions in water is another attractive area in chemistry, because water is a cheap, safe and an environmentally benign solvent [22].Multi-component reactions of arylglyoxals and enaminocarbonyls in the presence of different nucleophiles have been recently reported for synthesis of polyfunctionalized pyrroles [23][24][25]. However, to the best of our knowledge there are only a few reports on the simple addition of enaminocarbonyl compounds to arylglyoxals [26]. Caballero et al. reported the condensation of N-unsubstituted enaminoesters with phenylglyoxal to afford N-unsubstituted pyrroles. When N-phenyl-enaminoesters were used, they reported obtaining a complex mixture, from which the pyrrolinone derivative was isolated in 30 % yield. The mechanistic studies established the reversibility of the addition reaction between enaminoester and phenylglyoxal to afford the cyclic intermediate dihydroxy pyrrole and product pyrrolinone in reaction conditions [26]. In continuation of our previous studies on the application of arylglyoxals for the synthesis of heterocyclic compounds [27][28][29], here we wish to report a simple addition reaction between arylglyoxal monohydrates and enaminoketones in water as solvent at Abstract An efficient one-pot synthesis of 2H-pyrroline derivatives by a simple reaction of β-enaminocarbonyls with arylglyoxals in water at room temperature is reported. The addition reaction between arylglyoxal derivatives and β-enaminocarbonyls in water afforded 3,4-dihydroxy-2H-pyrrolines after about 10 min stirring at room temperature. When the reaction was done in the presence of aromatic amines, the corresponding 4-amino-5-hydroxy-2H-pyrroline derivatives were obtained in good yields. All reactions were performed in water at room temperature and the products were isolated by simple filtration.

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A multi-component domino reaction for the direct access to polyfunctionalized indolesvia intermolecular allylic esterification and indolation

Cited by 106 publications

References 43 publications

Regioselective Multicomponent Domino Reactions Providing Rapid and Efficient Routes to Fused Acridines

Regioselective Multicomponent Domino Reactions Providing Rapid and Efficient Routes to Fused Acridines

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

An efficient one-pot synthesis of polyfunctionalized 2H-pyrroline derivatives by reaction of β-enaminocarbonyls, arylglyoxals and amines

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