Premium
A Facile Synthesis of 4,6,7,8,8 a ,9‐Hexahydropyrrolo[1,2‐ a ][1,2,3]triazolo[1,5‐ d ]pyrazines by a Three‐Component Coupling Reaction Followed by Intramolecular 1,3‐Dipolar Cycloaddition
Author(s) -
Dhondge Attrimuni P.,
Afraj Shakil N.,
Nuzlia Cut,
Chen Chinpiao,
Lee GeneHsian
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300226
Subject(s) - chemistry , intramolecular force , cycloaddition , alkyne , catalysis , combinatorial chemistry , azide , stereochemistry , organic chemistry
A practical and efficient two‐step protocol for the synthesis of several new 4,6,7,8,8 a ,9‐hexahydropyrrolo[1,2‐ a ][1,2,3]triazolo[1,5‐ d ]pyrazines is described. The first step involves the AuBr 3 ‐catalyzed three‐component coupling reaction of terminal alkynes, aldehydes, and amines under solvent‐free conditions to provide the requisite propargylamines. The reaction tolerates a high structural diversity, requires only short reaction times, gives high diastereoselectivities, and is environmentally benign. Furthermore, the propargylamine products undergo catalyst‐free intramolecular azide–alkyne [3 + 2] dipolar cycloaddition reactions to give the 4,6,7,8,8 a ,9‐hexahydropyrrolo[1,2‐ a ][1,2,3]triazolo[1,5‐ d ]pyrazines in excellent yields and with excellent diastereoselectivities.