α-Oxoketene-S,S-, N,S- and N,N-acetals: Versatile intermediates in organic synthesis

Enaminones in heterocyclic synthesis

A facile, convenient, efficient, and high yielding synthesis of a combinatorial library of 3-aroylcoumarins has been developed by the condensation of easily available α-aroylketene dithioacetals (AKDTAs) and 2-hydroxybenzaldehydes (salicylaldehydes)/2-hydroxy-1-naphthaldehyde in the presence of catalytic amount of piperidine in THF reflux. The condensation of ferrocene derived α-aroylketene dithioacetal and 2-hydroxybenzaldehyde furnished coumarin installed on a ferrocene platform.

Condensation of α-Aroylketene Dithioacetals and 2-Hydroxyarylaldehydes Results in Facile Synthesis of a Combinatorial Library of 3-Aroylcoumarins#

[3+3] Benzannulations of benzenoid- and heteroaromatic-ring systems

3.02 – Imidazoles

Cycloaromatization of ∝-oxoketene dithioacetals with 3-methyl-5-lithiomethylisoxazole: A new general approach for synthesis of substituted and annelated 1,2-benzisoxazoles☆

Darzen's reaction on oxoketene dithioacetals: a new versatile synthesis of substituted and annelated furan-2-carboxylates

Synthese par cyclodeshydratation des α-hydroxyimino β-oxo N-methyldisubstitue benzenethiopropionimidates d'alkyle prepares par action du chlorure de nitrosyle sur les alkylthio-3 [methyldisubstitue amino]-3 acrylophenones

A facile general route to 2,2-disubstituted 5-alkylthio-4-aroyl-2H-imidazoles

The reaction of dimethyl N-aryl- or N-alkylcarbonimidodithioates with aminoacetaldehyde diethyl acetal in refluxing acetic acid affords 1-aryl or 1-alkyl-2-methylthioimidazoles in good yields. Dimethyl N-isopropylcarbonimidodithioate gave 1-isopropylimidazole-2(3H)-thione under similar conditions.

Reaction of Dimethyl N-Aryl- and N-Alkylcarbonimidodithioates with Aminoacetaldehyde Diethyl Acetal: A Direct Synthesis of 1-Aryl- and 1-Alkyl-2-methylthioimidazoles

A new route to 6-substituted 4a-e and 5,6-annulated 4f-l 1,2-benzisoxazoles has been developed through regioselective 1,2-nucleophilic addition of 5-lithiomethyl-3-methylisoxazole (2) to a variety of α -oxoketene dithioacetals 1a-l and subsequent cycloaromatization of the resulting hydroxyacetals in the presence of boron trifluoride -diethyl ether complex. The corresponding 4-dethiomethylated benzisoxazoles 6a-d were also synthesized by cyclocondensation of β-methylthio-α,β-unsaturated ketones with 2 under identical conditions. The reaction was further extended for the synthesis of (6-benzisoxazolyl)-substituted ethylenes 9a-e, butadienes 9f-g and hexatriene 9h by subjecting α-cinnamoyl ketene dithioacetals 7a-e and their higher enyl analogs 7f-h to similar transformations.

Cycloaromatization of α-Oxoketene Dithioacetals with 5-Lithiomethyl-3-methylisoxazole: A New General Method for the Synthesis of Substituted and Annulated 1,2-Benzisoxazoles

D. Pooranchand

Papers

Cycloaromatization of ∝-oxoketene dithioacetals with 3-methyl-5-lithiomethylisoxazole: A new general approach for synthesis of substituted and annelated 1,2-benzisoxazoles☆

Darzen's reaction on oxoketene dithioacetals: a new versatile synthesis of substituted and annelated furan-2-carboxylates

A facile general route to 2,2-disubstituted 5-alkylthio-4-aroyl-2H-imidazoles

Reaction of Dimethyl N-Aryl- and N-Alkylcarbonimidodithioates with Aminoacetaldehyde Diethyl Acetal: A Direct Synthesis of 1-Aryl- and 1-Alkyl-2-methylthioimidazoles

Cycloaromatization of α-Oxoketene Dithioacetals with 5-Lithiomethyl-3-methylisoxazole: A New General Method for the Synthesis of Substituted and Annulated 1,2-Benzisoxazoles