One-Pot Three-Component Synthesis of alpha -Iminonitriles by IBX/TBAB-Mediated Oxidative Strecker Reaction

The reaction of aldehydes, amines and TMSCN in the presence of 2-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) afforded alpha -iminonitriles, e.g. 4-MeOC6H4C(C==N):NCH2CH2Ph, in good to excellent yields under mild conditions. The presence of TBAB is essential for this transformation. The methodol. was applied to a two-step synthesis of indolizidine I via a microwave-assisted intramol. cycloaddn. of alpha -iminonitrile PhCH:CHC(C==N):N(CH2)3CH:CH2. [on SciFinder (R)]


Published in:
Organic Letters, 10, 8, 1509-1512
Year:
2008
Keywords:
Imines Role: SPN (Synthetic preparation) ; PREP (Preparation) (cyano ; alpha -iminonitriles; prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes ; amines and cyanotrimethylsilane ; and application to synthesis of an indolizidine); Strecker amino acid synthesis (oxidative; prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes ; amines and cyanotrimethylsilane ; and application to synthesis of an indolizidine); Multicomponent reaction (prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes ; amines and cyanotrimethylsilane ; and application to synthesis of an indolizidine); Aldehydes Role: RCT (Reactant) ; RACT (Reactant or reagent) (prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes ; amines and cyanotrimethylsilane ; and application to synthesis of an indolizidine); Amines Role: RCT (Reactant) ; RACT (Reactant or reagent) (primary; prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes ; amines and cyanotrimethylsilane ; and application to synthesis of an indolizidine) ; aldehyde amine cyanotrimethylsilane IBX tetrabutylammonium bromide multicomponent oxidative Strecker; alpha iminonitrile prepn iodoxybenzoic acid tetrabutylammonium bromide; iminonitrile alpha microwave intramol cycloaddn; indolizidine prepn
Note:
CAN 148:471264
21-2
General Organic Chemistry
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1523-7060
written in English.
1019849-95-6P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (crystal structure; prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes, amines and cyanotrimethylsilane, and application to synthesis of an indolizidine); 62-53-3 (Aniline); 64-04-0 (Benzeneethanamine); 75-64-9; 78-84-2 (Isobutanal); 83-38-5; 100-52-7 (Benzaldehyde); 104-53-0 (Benzenepropanal); 104-55-2 (Cinnamaldehyde); 104-94-9; 111-71-7 (Heptanal); 123-11-5; 500-22-1 (3-Pyridinecarboxaldehyde); 765-30-0 (Cyclopropylamine); 2100-17-6 (4-Pentenal); 2627-86-3 (Benzenemethanamine, alpha -methyl-,(S)-); 22537-07-1 (4-Penten-1-amine); 125654-82-2 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes, amines and cyanotrimethylsilane, and application to synthesis of an indolizidine); 1019850-02-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes, amines and cyanotrimethylsilane, and application to synthesis of an indolizidine); 1643-19-2 (Tetrabutylammonium bromide); 7677-24-9 (Cyanotrimethylsilane); 64297-64-9 (2-Iodoxybenzoic acid) Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes, amines and cyanotrimethylsilane, and application to synthesis of an indolizidine); 4686-14-0P; 1019849-88-7P; 1019849-89-8P; 1019849-90-1P; 1019849-91-2P; 1019849-92-3P; 1019849-93-4P; 1019849-94-5P; 1019849-96-7P; 1019849-97-8P; 1019849-98-9P; 1019849-99-0P; 1019850-00-0P; 1019850-01-1P; 1019850-03-3P; 1019850-04-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydes, amines and cyanotrimethylsilane, and application to synthesis of an indolizidine)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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