Modulating the reactivity of alpha -isocyanoacetates: multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones
The reactivity pattern of alpha -isocyanoacetates can be tuned by modulating the acidity of the alpha C-H bond(s) against the nucleophilicity of the conjugate base. Three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate (I) are described. E.g., reaction of I, morpholine, and cyclohexanal gave 92% 5-methoxyoxazole II. [on SciFinder (R)]
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Bonne, D., Dekhane, M., & Zhu, J. (2007). Modulating the reactivity of alpha -isocyanoacetates: multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones. Angewandte Chemie International Edition, 46(14), 2485–2488. https://doi.org/10.1002/anie.200605005
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2007
46
14
2485
2488
CAN 147:30998
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
50-00-0 (Formaldehyde); 78-84-2 (Isobutanal); 91-21-4; 100-46-9 (Benzylamine); 100-52-7 (Benzaldehyde); 100-61-8 (N-Methylaniline); 104-53-0 (3-Phenylpropanal); 109-73-9 (Butylamine); 110-91-8 (Morpholine); 111-71-7 (Heptanal); 120-20-7; 122-78-1 (Benzeneacetaldehyde); 123-75-1 (Pyrrolidine); 350-46-9 (4-Fluoronitrobenzene); 506-59-2 (Dimethylamine hydrochloride); 637-44-5 (3-Phenylpropiolic acid); 2043-61-0 (Cyclohexanal); 39687-95-1 (Methyl alpha -isocyanoacetate); 135284-85-4; 939047-23-1; 939047-24-2 Role: RCT (Reactant), RACT (Reactant or reagent) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate); 7299-58-3P; 939047-03-7P; 939047-12-8P; 939047-22-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate); 939047-04-8P; 939047-05-9P; 939047-06-0P; 939047-07-1P; 939047-08-2P; 939047-09-3P; 939047-10-6P; 939047-11-7P; 939047-13-9P; 939047-14-0P; 939047-15-1P; 939047-16-2P; 939047-17-3P; 939047-18-4P; 939047-19-5P; 939047-20-8P; 939047-21-9P Role: SPN (Synthetic preparation), PREP (Preparation) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate)
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