ChemInform Abstract: SYNTHESIS OF 1,3‐OXAZINE‐2,4‐DIONES

Lapkin, I. I.; Semenov, V. I.; Saitkulova, F. G.

doi:10.1002/chin.198311232

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“…Though high-yielding in some cases, these syntheses require at least two steps and necessarily generate byproducts. The latter is also true of OD syntheses in which a β-hydroxy or β-metalloxy ester is condensed with an isocyanate (Scheme , path b) . Recently, OD synthesis has been reported via the base-mediated (and, in some cases, metal-catalyzed) rearrangement of β-hydroxy N -acyloxazolidin-2-ones, which are the aldol products of N -acyloxazolidin-2-ones (Scheme , path c), 5a,b,,, and by similar rearrangements .…”

Section: Introductionmentioning

confidence: 95%

A New Multicomponent Reaction Catalyzed by a [Lewis Acid]⁺[Co(CO)₄]^- Catalyst: Stereospecific Synthesis of 1,3-Oxazinane-2,4-diones from Epoxides, Isocyanates, and CO

et al. 2007

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The use of mechanistic information to develop a new, catalytic multicomponent reaction is described. The complex [(salph)Al(THF)2]+[Co(CO)4]- (1, salph = N,N'-o-phenylenebis(3,5-di-tert-butylsalicylideneimine), THF = tetrahydrofuran), which is known to carbonylate epoxides, aziridines, and beta-lactones, was used to catalyze the synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO. Under optimized conditions, the reaction was both selective and high-yielding. 1,3-Oxazinane-2,4-diones were synthesized from a variety of epoxides and isocyanates, including some epoxides that do not undergo simple ring-expansion carbonylation. The best results were obtained using highly electrophilic isocyanates. The mechanism of the multicomponent reaction was investigated using labeling and stereochemistry, and the data obtained were consistent with the 1-catalyzed formation of beta-lactone and 1,3-oxazinane-2,4-dione from a common intermediate.

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Section: Introductionmentioning

confidence: 95%

A New Multicomponent Reaction Catalyzed by a [Lewis Acid]⁺[Co(CO)₄]^- Catalyst: Stereospecific Synthesis of 1,3-Oxazinane-2,4-diones from Epoxides, Isocyanates, and CO

et al. 2007

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ChemInform Abstract: SYNTHESIS OF 1,3‐OXAZINE‐2,4‐DIONES

Cited by 1 publication

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A New Multicomponent Reaction Catalyzed by a [Lewis Acid]⁺[Co(CO)₄]^- Catalyst: Stereospecific Synthesis of 1,3-Oxazinane-2,4-diones from Epoxides, Isocyanates, and CO

A New Multicomponent Reaction Catalyzed by a [Lewis Acid]⁺[Co(CO)₄]^- Catalyst: Stereospecific Synthesis of 1,3-Oxazinane-2,4-diones from Epoxides, Isocyanates, and CO

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ChemInform Abstract: SYNTHESIS OF 1,3‐OXAZINE‐2,4‐DIONES

Cited by 1 publication

References 0 publications

A New Multicomponent Reaction Catalyzed by a [Lewis Acid]+[Co(CO)4]- Catalyst: Stereospecific Synthesis of 1,3-Oxazinane-2,4-diones from Epoxides, Isocyanates, and CO

A New Multicomponent Reaction Catalyzed by a [Lewis Acid]+[Co(CO)4]- Catalyst: Stereospecific Synthesis of 1,3-Oxazinane-2,4-diones from Epoxides, Isocyanates, and CO

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A New Multicomponent Reaction Catalyzed by a [Lewis Acid]⁺[Co(CO)₄]^- Catalyst: Stereospecific Synthesis of 1,3-Oxazinane-2,4-diones from Epoxides, Isocyanates, and CO

A New Multicomponent Reaction Catalyzed by a [Lewis Acid]⁺[Co(CO)₄]^- Catalyst: Stereospecific Synthesis of 1,3-Oxazinane-2,4-diones from Epoxides, Isocyanates, and CO