Novel Synthesis of Substituted Pyrrole Bound to Indolinone via Molecular Iodine-Catalyzed Reaction

Banik, Bimal K.; Garcia, Isabella; Morales, Frances R.; Aguilar, Calista

doi:10.1515/hc.2007.13.2-3.109

Cited by 10 publications

(7 citation statements)

References 14 publications

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“…We hypothesized that our work on iodine-catalyzed [ 11 , 12 , 13 , 14 , 15 , 16 ] reactions on acetal and glycosylation might prove useful for the facile synthesis of pyrroles under mild conditions. The methoxy groups in 2,5-dimethoxytetrahydrofuran ( 1 ) can be deprotected under mild acidic conditions and microwave irradiation.…”

Section: Resultsmentioning

confidence: 99%

An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions

Bandyopadhyay¹,

Mukherjee²,

Banik³

2010

Molecules

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Section: Resultsmentioning

confidence: 99%

An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions

Bandyopadhyay¹,

Mukherjee²,

Banik³

2010

Molecules

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“…The presence of small amounts of iodine (5 mol%) is necessary for the success of the reaction. The same has been studied extensively in our laboratory in several iodine-catalyzed reactions [ 26 , 27 , 28 , 29 , 30 , 31 ].…”

Section: Resultsmentioning

confidence: 99%

Remarkable Iodine-Catalyzed Synthesis of Novel Pyrrole- Bearing N-Polyaromatic β-Lactams

Bandyopadhyay¹,

Rivera²,

Salinas³

et al. 2010

Molecules

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Because of their interesting biological properties various methods for the synthesis of substituted pyrroles are described in the literature. However, synthesis of pyrroles fused with a β-lactam ring has not been reported. Our group has demonstrated synthesis and biological evaluation of various β-lactams as anticancer agents. The anticancer activities of these compounds have prompted us to study the synthesis of pyrroles bound to the β-lactams. We have identified an expeditious synthetic method for the preparation of pyrroles fused with β-lactams by reacting 3-amino β-lactams with acetonylacetone in the presence of catalytic amounts (5 mol%) of molecular iodine at room temperature. It has also been discovered that the reaction gives products under domestic and automated microwave oven irradiation. To our knowledge, there are no other prior reports that describe the synthesis of pyrrole-substituted β-lactams.

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“…Molecular iodine was successful in catalyzing the reaction between isatin and hydoxyproline derivatives to form pyrrole-fused oxoindoles in high yield [5]. It was believed that the amino acid group of proline reacted with the keto group of isatin and formed a cyclic intermediate.…”

Section: Condensed Heterocyclesmentioning

confidence: 99%

Molecular Iodine-Catalyzed Reactions: Our Own Account

Banik¹

2017

Mod Chem Appl

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Novel Synthesis of Substituted Pyrrole Bound to Indolinone via Molecular Iodine-Catalyzed Reaction

Cited by 10 publications

References 14 publications

An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions

An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions

Remarkable Iodine-Catalyzed Synthesis of Novel Pyrrole- Bearing N-Polyaromatic β-Lactams

Molecular Iodine-Catalyzed Reactions: Our Own Account

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