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Synthesis of N‐Fused Indolines via Copper (II)‐Catalyzed Dearomatizing Cyclization of Indoles
Author(s) -
Zhang Jingyu,
Xia Wei,
Huda Saskia,
Ward Jas S.,
Rissanen Kari,
Albrecht Markus
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.202100290
Subject(s) - chemistry , amination , yield (engineering) , catalysis , copper , combinatorial chemistry , bond cleavage , cleavage (geology) , medicinal chemistry , organic chemistry , materials science , geotechnical engineering , engineering , metallurgy , fracture (geology)
Herein, a copper(II)‐catalyzed dearomative cyclization amination of N‐(2‐aminobenzoyl) indoles is presented. Under mild reaction conditions, the cyclization proceeds to afford tetracyclic indolines by forming a new C−N bond in good yields. The tetracyclic 5a,6‐dihydroindolo[2,1‐b]quinazolin‐12(5H)‐ones are obtained in good to excellent yields (up to 99% yield) by using trifluoromethanesulfonic acid (TfOH) mediated N−Ts bond cleavage. The obtained compounds could be easily functionalized by simple synthetic methods.