A three-component reaction between dimethyl acetylenedicarboxylate (DMAD) and trialkyl phosphites in the presence of N-aryl-3-hydroxynaphthalene-2-carboxamide leads to dialkyl 2-(dimethoxyphosphoryl)-3-[2-hydroxy-3-(arylcarbamyl)naphthalen-1-yl] succinate in excellent yields. A similar reaction with triphenylphosphine, instead of phosphites, produces dimethyl 2-[2-hydroxy-3-(arylcarbamoyl)naphthalen-1-yl]maleates. In the absence of triphenylphosphine or phosphite, DMAD adds to N-aryl-3-hydroxynaphthalene-2-carboxamide to produce alkyl 2-(alkoxycarbonylmethyl)-4-oxo-3-aryl-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-2-carboxylates in good yields.
Ninhydrin reacts with amides in ethanol to produce N- (2-hydroxy-1,3-dioxoindan-2-yl)amide derivatives in nearly quantitative yields. Reaction between these adducts and electron-deficient acetylenic esters in the presence of triphenylphosphine leads to dialkyl 8a-acetylamino-8-oxo-8,8a-dihydro-2H-1-oxacyclopenta[α]indene-2,3-dicarboxylate derivatives in good yields.
Multicomponent reactions O 0359 A Three-Component Reaction Between Trialkyl Phosphites or Triphenylphosphine, Dimethyl Acetylenedicarboxylate and N-Aryl-3-hydroxynaphtha-lene-2-carboxamide. -(ANARY-ABBASINEJAD*, M.; HASSANABADI, A.; MAZRAEH-SEFFID, M.; J. Chem. Res. 2007, 12, 708-712; Dep. Chem., Islamic Azad Univ., Yazd, Iran; Eng.) -A. Forchert 25-056
2,4,6-Triarylpyridine derivatives were synthesised by the reaction of guanidine with an acetophenone and a chalcone. These reactions were carried out as economical one-pot reactions under green conditions: no catalyst and solvent free.
The microwave assisted reaction between a chalcone, an acetophenone and guanidine as alternative ammonia source provides a simple one‐pot access to 2,4,6‐triarylpyridines (III).
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