Synthesis of Pyrroles by Consecutive Multicomponent Reaction/[4 + 1] Cycloaddition of alpha -Iminonitriles with Isocyanides
2009
Abstract
[4 + 1] Cycloaddn. of alpha ,beta -unsatd. imidoyl cyanide (2-cyano-1-azadienes) with isocyanides in the presence of a catalytic amt. of AlCl3 afforded polysubstituted 2-amino-5-cyanopyrroles in good to excellent yields. In combination with the IBX/TBAB-mediated oxidative Strecker reaction, this important heterocycle is readily synthesized in two steps from simple starting materials. [on SciFinder (R)]
Details
Title
Synthesis of Pyrroles by Consecutive Multicomponent Reaction/[4 + 1] Cycloaddition of alpha -Iminonitriles with Isocyanides
Author(s)
Fontaine, Patrice ; Masson, Geraldine ; Zhu, Jieping
Published in
Organic Letters
Volume
11
Issue
7
Pages
1555-1558
Date
2009
ISSN
1523-7060
Keywords
Cycloaddition reaction; Cycloaddition reaction catalysts ([4+1]; prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); Nitriles Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (imino; prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); Amines Role: RCT (Reactant); RACT (Reactant or reagent) (multicomponent oxidative Strecker reaction of alpha; beta -unsatd. aldehydes; amines; and trimethylsilyl cyanide in presence of IBX and TBAB); Strecker amino acid synthesis (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); Isocyanides Role: RCT (Reactant); RACT (Reactant or reagent) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); Aldehydes Role: RCT (Reactant); RACT (Reactant or reagent) (alpha; beta -unsatd.; multicomponent oxidative Strecker reaction of alpha; beta -unsatd. aldehydes; amines; and trimethylsilyl cyanide in presence of IBX and TBAB); aminocyanopyrrole prepn; pyrrole aminocyano prepn; oxidative Strecker reaction cycloaddn imino nitrile isocyanide
Note
CAN 150:351858
27-10
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
7446-70-0 (Aluminum chloride (AlCl3) Role: CAT (Catalyst use), USES (Uses) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 64-04-0 (Phenethylamine); 123-73-9; 497-03-0; 765-30-0 (Cyclopropylamine); 931-53-3 (Cyclohexyl isocyanide); 2769-71-3 (2,6-Dimethylphenyl isocyanide); 7188-38-7 (tert-Butyl isocyanide); 7677-24-9 (Trimethylsilyl cyanide); 10340-91-7 (Benzyl isocyanide); 14371-10-9; 24954-67-4 (4-Nitrophenethylamine) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 1019849-91-2P; 1134284-80-2P; 1134284-81-3P; 1134284-82-4P; 1134284-83-5P; 1134284-89-1P; 1134284-91-5P; 1134284-92-6P; 1134284-93-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 1643-19-2 (TBAB); 64297-64-9 Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 1134284-84-6P; 1134284-85-7P; 1134284-86-8P; 1134284-87-9P; 1134284-88-0P; 1134284-90-4P; 1134284-94-8P; 1134284-95-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 67434-29-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of alpha -isocyanoacetamide deriv. with alpha -iminonitrile); 1134284-96-0P; 1134284-97-1P Role: SPN (Synthetic preparation), PREP (Preparation) (reaction of alpha -isocyanoacetamide deriv. with alpha -iminonitrile)
27-10
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
7446-70-0 (Aluminum chloride (AlCl3) Role: CAT (Catalyst use), USES (Uses) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 64-04-0 (Phenethylamine); 123-73-9; 497-03-0; 765-30-0 (Cyclopropylamine); 931-53-3 (Cyclohexyl isocyanide); 2769-71-3 (2,6-Dimethylphenyl isocyanide); 7188-38-7 (tert-Butyl isocyanide); 7677-24-9 (Trimethylsilyl cyanide); 10340-91-7 (Benzyl isocyanide); 14371-10-9; 24954-67-4 (4-Nitrophenethylamine) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 1019849-91-2P; 1134284-80-2P; 1134284-81-3P; 1134284-82-4P; 1134284-83-5P; 1134284-89-1P; 1134284-91-5P; 1134284-92-6P; 1134284-93-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 1643-19-2 (TBAB); 64297-64-9 Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 1134284-84-6P; 1134284-85-7P; 1134284-86-8P; 1134284-87-9P; 1134284-88-0P; 1134284-90-4P; 1134284-94-8P; 1134284-95-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); 67434-29-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of alpha -isocyanoacetamide deriv. with alpha -iminonitrile); 1134284-96-0P; 1134284-97-1P Role: SPN (Synthetic preparation), PREP (Preparation) (reaction of alpha -isocyanoacetamide deriv. with alpha -iminonitrile)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25