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Substituted 1 H ‐1,2,3‐Triazol‐4‐yl‐1 H ‐pyrrolo[2,3‐b]pyridines by De Novo One‐Pot Ring‐Forming Coupling/Cyclization/Desilylation Cu Alkyne/Azide Cycloaddition (AAC) Sequence
Author(s) -
Lessing Timo,
van Mark Hauke,
Müller Thomas J. J.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801632
Subject(s) - alkyne , cycloaddition , chemistry , ring (chemistry) , azide , triazole , stereochemistry , combinatorial chemistry , sequence (biology) , catalysis , one pot synthesis , silylation , organic chemistry , biochemistry
Substituted 1 H ‐1,2,3‐triazol‐4‐yl‐pyrrolo[2,3‐b]pyridines are efficiently prepared by a one‐pot coupling/cyclization/desilylation Cu alkyne/azide cycloaddition (CuAAC) sequence in the sense of a consecutive three‐component fashion. The key feature of this new de novo formation of azole and triazole anellation is the sequentially Pd/Cu‐catalyzed process employing tri(iso‐propyl)silyl (TIPS) butadiyne as a four‐carbon building block. In addition, the sequence can be expanded in a four‐component fashion also employing the in situ formation of the required azides.