Bonne, DamienDekhane, MouloudZhu, Jieping2010-11-252010-11-252010-11-25200510.1021/ol052239whttps://infoscience.epfl.ch/handle/20.500.14299/58475A 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)]Aldehydes Role: RCT (Reactant)RACT (Reactant or reagent) (aliph.; prepn. of aminoalkyl-substituted (imino)benzoxazines and derivs. via three-component coupling of o-isocyanobenzamides with aldehydes and amines); Amides Role: RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (aryl; prepn. of aminoalkyl-substituted (imino)benzoxazines and derivs. via three-component coupling of o-isocyanobenzamides with aldehydes and amines); Amines 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); Isocyanides 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); Coupling reaction (three-component; prepn. of aminoalkyl-substituted (imino)benzoxazines and derivs. via three-component coupling of o-isocyanobenzamides with aldehydes and amines)benzoxazine imino multicomponent synthesis; benzamide isocyano prepn three component coupling aldehyde amine; isonitrile amide prepn three component coupling aldehyde aminetext::journal::journal article::research article