research article

Exploiting the Dual Reactivity of o-Isocyanobenzamide: Three-Component Synthesis of 4-Imino-4H-3,1-benzoxazines

Bonne, Damien
•
Dekhane, Mouloud
•
Zhu, Jieping  
2005
Organic Letters

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)]

Type
research article
DOI
10.1021/ol052239w
Author(s)
Bonne, Damien
Dekhane, Mouloud
Zhu, Jieping  
Date Issued

2005

Published in
Organic Letters
Volume

7

Issue

23

Start page

5285

End page

5288

Subjects

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 amine

Note

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58475