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)]
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Pirali, T., Tron, G. C., & Zhu, J. (2006). One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloaddition. Organic Letters, 8(18), 4145–4148. https://doi.org/10.1021/ol061782p
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2006
8
18
4145
4148
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.)
REVIEWED
OTHER