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Copper(I)‐Catalyzed Intramolecular Cyclization of o ‐Propargyloxy Diketopiperazines to Access Diverse Diazabicyclic and Spiro‐Diketopiperazinochromanes
Author(s) -
Manavi Bita,
Tejeneki Hossein Zahedian,
Rominger Frank,
Armaghan Mahsa,
Frank Walter,
Bijanzadeh Hamid Reza,
Balalaie Saeed
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100432
Subject(s) - diketopiperazines , alkyne , intramolecular force , chemistry , moiety , cycloaddition , azomethine ylide , catalysis , ylide , copper , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , 1,3 dipolar cycloaddition
In this report, two distinctive intramolecular cyclizations of o ‐propargyloxy diketopiperazines (achieved from a one‐pot Ugi post‐transformation) is achieved via a copper(I)‐catalyzed intramolecular reaction of azomethine ylide and alkyne moiety. The presence of internal alkyne in the starting materials directed the reaction towards through [3+2]‐cycloaddition, while terminal alkyne led to a spirocyclization reaction between azomethine ylide and terminal unsaturated C−C bond. This method offering an opportunity for the synthesis of challenging Diazabicyclics and Spiro‐Diketopiperazinochromanes in high yields with exclusive diastereoselectivity.