One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloaddition
Pirali, Tracey; Tron, Gian Cesare; Zhu, Jieping
2006

Abstract

By combining three appropriately designed simple substrates, a programmed sequence involving an alpha -isocyano acetamide-based three-component reaction followed by a copper-catalyzed intramol. [3+2] cycloaddn. of alkyne and azide took place to afford complex macrocycles, e.g., I, in moderate to good yields. One macrocycle and two heterocycles were produced with concurrent formation of five chem. bonds in this operationally simple process. [on SciFinder (R)]

Details

Title One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloaddition
Author(s) Pirali, Tracey ; Tron, Gian Cesare ; Zhu, Jieping
Published in Organic Letters
Volume 8
Issue 18
Pages 4145-4148
Date 2006
ISSN 1523-7060
Keywords
Cycloaddition reaction ([3+2]; one-pot prepn. of macrocycles via tandem three-component reaction of aldehydes; amines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Alcohols Role: RCT (Reactant); RACT (Reactant or reagent) (alkynyl; one-pot prepn. of macrocycles via tandem three-component reaction of aldehydes; amines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Amidation; Heterocyclization; Macrocyclization (one-pot prepn. of macrocycles via tandem three-component reaction of aldehydes; amines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Aldehydes; Alkynes; Amides; Amines; Azides; Isocyanates Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (one-pot prepn. of macrocycles via tandem three-component reaction of aldehydes; amines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Macrocyclic compounds Role: SPN (Synthetic preparation); PREP (Preparation) (one-pot prepn. of macrocycles via tandem three-component reaction of aldehydes; amines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); Coupling reaction (three-component; one-pot prepn. of macrocycles via tandem three-component reaction of aldehydes; amines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); azidoamine alkynyl isocyanoacetamide aldehyde tandem coupling intramol cycloaddn copper; macrocycle tricyclo oxazolyl triazolyl deriv prepn; copper tandem coupling intramol cycloaddn catalyst
Note CAN 145:397493
28-23
Heterocyclic Compounds (More Than One Hetero Atom)
Dipartimento di Scienze Chimiche Alimentari Farmaceutiche e Farmacologiche and Drug and Food Biotechnology Center,Universita degli Studi del Piemonte Orientale "A. Avogadro",Novara,Italy.
Journal
written in English.
100-46-9 (Benzylamine); 110-91-8 (Morpholine); 111-71-7 (Heptanal); 302-72-7 (Alanine); 555-16-8 (4-Nitrobenzaldehyde); 5390-04-5 (4-Pentyn-1-ol); 13200-85-6 (N-Formyl-phenylalanine); 13734-36-6; 35161-71-8; 54005-84-4 (7-Bromoheptanal); 63478-76-2 (6-Heptyn-1-ol); 121667-78-5; 150651-47-1; 389131-94-6 Role: RCT (Reactant), RACT (Reactant or reagent) (one-pot prepn. of macrocycles via tandem three-component reaction of aldehydes, amines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); 5893-10-7P; 67100-10-1P (6-Heptynal); 77758-50-0P; 143427-45-6P; 909402-08-0P; 911306-03-1P; 911306-04-2P; 911306-05-3P; 911306-06-4P; 911306-18-8P; 911306-19-9P; 911306-20-2P; 911306-21-3P; 911306-22-4P; 911306-23-5P; 911306-51-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (one-pot prepn. of macrocycles via tandem three-component reaction of aldehydes, amines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.); 911306-07-5P; 911306-08-6P; 911306-09-7P; 911306-10-0P; 911306-11-1P; 911306-13-3P; 911306-14-4P; 911306-15-5P; 911306-16-6P; 911306-17-7P Role: SPN (Synthetic preparation), PREP (Preparation) (one-pot prepn. of macrocycles via tandem three-component reaction of aldehydes, amines and alkynyl(isocyano)acetamides followed by copper-catalyzed intramol. [3+2] cycloaddn.)
DOI https://doi.org/10.1021/ol061782p
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
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Record creation date 2010-11-25