One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloaddition

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)]


Published in:
Organic Letters, 8, 18, 4145-4148
Year:
2006
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
1523-7060
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.)
Laboratories:




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


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