Organometallic addition to N-(N-acyl-N-methylamino)cycloimminium salts: a general method for ketone synthesis

Heras, Maria A. de las; Molina, A.; Vaquero, Juan J.; Navio, J. L. Garcia; Alvárez‐Builla, Julio

doi:10.1021/jo00073a059

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Benzo-13-azoles2

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Cited by 19 publications

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“…The synthesis of 1-amino-3-alkylimidazolium 284 [461] and N-imidazolium-Nmethyl-amides 286 [462] has been reported. In the first case, the salts are obtained by direct amination of the corresponding alkoxycarbonylazoles using mesitylenesulfonylhydroxylamine (MSH) as the aminating agents (Scheme 10.162).…”

Section: Benzo-13-azolesmentioning

confidence: 99%

“…2-Alkoxycarbonylazolium N-ylides-N-aminides 289 are species that have the potential to act as efficient 1,4-dipole equivalents when they react with heterocumulenes such as iso(thio)cyanates and carbodiimides [465]. N-Imidazolium-N-methylamides and bis-amides behave as highly selective acylating reagents towards organometallics, leading to ketones [462] and diketones. The metallation of alkoxycarbonyl-N-imidazolium-N-methyl amides with LDA followed by the addition of a Grignard reagent affords 4-oxo and homologous esters (Scheme 10.163).…”

Section: Benzo-13-azolesmentioning

confidence: 99%

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