Novel and Convenient One-Pot Synthesis of Fused Ring Heterocycles From 1,2-Diketones and Phosphorodichloridate and Phosphorothiodichloridate

Singh, Maya Shankar; Mishra, Geeta; Mehrotra, K. N.

doi:10.1080/10426509108029441

Cited by 15 publications

(6 citation statements)

References 7 publications

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“…62 Treatment of N-methylisatin (53) with sodium in dry tetrahydrofuran (THF) followed by addition of phosphorodichloridates 56 (Z ) O; R ) Et, Ph) and phosphorothiodichloridates 53 (Z ) S, R ) Et, Ph) gives the dioxaphospholes 57. 63 The synthesis involves the initial formation of diradical dianion 54, by electron transfer from sodium to diketones 53 by radical coupling to give the dianion 55. 64 Similar reaction of acenaphthenequinone with 56 yields the corresponding dioxaphospholes 58.…”

Section: Hexafluorobiacetyl (50) Reacts With Phosphorus Fluorides 51mentioning

confidence: 99%

Reactions of α-Diketones ando-Quinones with Phosphorus Compounds

2002

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Section: Hexafluorobiacetyl (50) Reacts With Phosphorus Fluorides 51mentioning

confidence: 99%

Reactions of α-Diketones ando-Quinones with Phosphorus Compounds

2002

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“…Cyclic indolic phosphates were obtained when 1-methylisatin was reduced with sodium in THF to yield a dianion that subsequently reacted with alkyl phosphorodichloridates 373 (Scheme 94).…”

Section: Oxygen Sulfur and Phosphorous Nucleophilesmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

447

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Isatinas (1H-indol-2,3-diona) são compostos de grande versatilidade sintética, podendo ser utilizados na obtenção de diversos sistemas heterociclos, como derivados indólicos e quinolínicos, o que as tornam importantes matérias-primas na síntese de fármacos. Isatinas também têm sido detectadas em tecidos de mamíferos, o que tem despertado o interesse em seu estudo como moduladores em diversos processos bioquímicos. Os avanços na aplicação de isatinas em síntese orgânica, bem como na compreensão de seus efeitos biológicos e farmacológicos nos últimos vinte e cinco anos encontram-se relatados nesta revisão e seus respectivos materiais suplementares.Isatins (1H-indole-2,3-dione) are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as raw material for drug synthesis. Isatins have also been found in mammalian tissue and their function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatins for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information.

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“…64 This addition reaction of α-diazophosphoryl compounds 44 at position 3 of isatin with subsequent ring expansion was also applicable to derivatives of indane-2,3-dione, benzofuran-2,3-dione, and pyrrole-2,3-dione, and was used to obtain compounds 45, 46. The reaction with benzothiophene-2,3-dione occurred at position 2 and produced α-diazophosphonates 47.…”

Section: Scheme 15mentioning

confidence: 99%