Exploiting the Dual Reactivity of o-Isocyanobenzamide: Three-Component Synthesis of 4-Imino-4H-3,1-benzoxazines
A multicomponent synthesis of 4-imino-4H-3,1-benzoxazines I [R1 = H, MeO; R2 = n-Bu, PhCH2, PhCH2CH2, (S)-PhCH2CH(CO2Me), etc.; R3 = H, Me2CH, cyclohexyl, n-hexyl; R4 = H, R5 = n-Bu, MeO2CCH2CH2, PhCH2, 9-fluorenylmethyl; R4 = R5 = Me; R4R5N = morpholino] is developed. Heating a toluene soln. of an aldehyde R3CHO, an amine R4R5NH, and an isonitrile II in the presence of a stoichiometric amt. of ammonium chloride at 60 DegC for 12 h produces the benzoxazines I in good to excellent yields. [on SciFinder (R)]
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Bonne, D., Dekhane, M., & Zhu, J. (2005). Exploiting the Dual Reactivity of o-Isocyanobenzamide: Three-Component Synthesis of 4-Imino-4H-3,1-benzoxazines. Organic Letters, 7(23), 5285–5288. https://doi.org/10.1021/ol052239w
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2005
7
23
5285
5288
CAN 144:36301
28-13
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
64-04-0 (Phenethylamine); 78-84-2 (Isobutanal); 100-46-9 (Benzylamine); 109-73-9 (1-Butylamine); 110-91-8 (Morpholine); 111-71-7 (Heptanal); 118-48-9 (Isatoic anhydride); 2043-61-0 (Cyclohexanecarboxaldehyde); 6057-90-5; 6705-03-9 (2-Amino-5-methoxybenzoic acid); 34221-61-9; 870672-30-3; 870672-31-4; 870672-32-5 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of aminoalkyl-substituted (imino)benzoxazines and derivs. via three-component coupling of o-isocyanobenzamides with aldehydes and amines); 5471-20-5P; 10494-82-3P; 37795-77-0P; 870672-06-3P; 870672-07-4P; 870672-08-5P; 870672-09-6P; 870672-10-9P; 870672-11-0P; 870672-12-1P; 870672-20-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of aminoalkyl-substituted (imino)benzoxazines and derivs. via three-component coupling of o-isocyanobenzamides with aldehydes and amines); 870672-13-2P; 870672-14-3P; 870672-15-4P; 870672-16-5P; 870672-17-6P; 870672-18-7P; 870672-19-8P; 870672-21-2P; 870672-22-3P; 870672-23-4P; 870672-24-5P; 870672-25-6P; 870672-26-7P; 870672-27-8P; 870672-28-9P; 870672-29-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of aminoalkyl-substituted (imino)benzoxazines and derivs. via three-component coupling of o-isocyanobenzamides with aldehydes and amines)
REVIEWED
OTHER