TY - JOUR
T1 - Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts
T2 - Access to the azepino[3,4,5-cd]indoles and spiroindolines
AU - Zaman, Manzoor
AU - Hasan, Muhammad
AU - Peshkov, Anatoly A.
AU - Puzyk, Aleksandra
AU - Wang, Yuqing
AU - Lim, Chang Keun
AU - Pereshivko, Olga P.
AU - Peshkov, Vsevolod A.
N1 - Publisher Copyright:
© 2023 Elsevier Ltd
PY - 2023/10/25
Y1 - 2023/10/25
N2 - 4-Bromo-1H-indole-3-carbaldehyde has been explored as a key building block for a post-Ugi assembly of azepino[3,4,5-cd]indoles and spiroindolines. First, the corresponding Ugi adducts were successfully employed in palladium-catalyzed reductive Heck cyclization producing a range of azepinoindoles. Then, 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts were subjected to cationic gold catalysis affording tetracyclic spiroindolines. Furthermore, the aryl bromide moiety retained in the resulting spiroindolines was found to be amendable to further functionalization via Suzuki and Sonogashira couplings.
AB - 4-Bromo-1H-indole-3-carbaldehyde has been explored as a key building block for a post-Ugi assembly of azepino[3,4,5-cd]indoles and spiroindolines. First, the corresponding Ugi adducts were successfully employed in palladium-catalyzed reductive Heck cyclization producing a range of azepinoindoles. Then, 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts were subjected to cationic gold catalysis affording tetracyclic spiroindolines. Furthermore, the aryl bromide moiety retained in the resulting spiroindolines was found to be amendable to further functionalization via Suzuki and Sonogashira couplings.
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U2 - 10.1016/j.tetlet.2023.154769
DO - 10.1016/j.tetlet.2023.154769
M3 - Article
AN - SCOPUS:85173553945
SN - 0040-4039
VL - 130
JO - Tetrahedron Letters
JF - Tetrahedron Letters
M1 - 154769
ER -