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Synthesis of New Chiral Triazoles Linked 1,5‐Benzodiazepine Conjugates via Copper‐Catalyzed 1,3‐Dipolar Cycloaddition Reaction
Author(s) -
Haouas Amel,
Mtiraoui Hasan,
Bouzayani Nadia,
Ibrahim Sana,
Marque Sylvain,
Hajji Melek,
BelHadjTahar Radhouane,
Msaddek Moncef
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202004276
Subject(s) - moiety , cycloaddition , alkyne , 1,3 dipolar cycloaddition , chemistry , conjugate , azide , catalysis , combinatorial chemistry , copper , stereochemistry , organic chemistry , mathematical analysis , mathematics
Abstract A simple synthesis of 1,4‐disubstituted 1,2,3‐triazoles linked‐1,5‐benzodiazepinones was performed via a Cu(I)‐catalyzed 1,3‐dipolar alkyne‐azide coupling reaction (CuAAC). A new chiral 1,5‐benzodiazepine conjugates moiety containing alkyne spacers is designed and used as dipoles to give the access to the target cycloadducts with high yields. Both chiral center and freeze conformations allow to reach important diastereoselectivity from 70 up to 100 %.