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N ‐Heterocyclic‐Carbene‐Catalyzed Reaction of α‐Bromo‐α,β‐Unsaturated Aldehyde or α,β‐Dibromoaldehyde with Isatins: An Efficient Synthesis of Spirocyclic Oxindole–Dihydropyranones
Author(s) -
Yao Changsheng,
Xiao Zhaoxin,
Liu Rui,
Li Tuanjie,
Jiao Weihui,
Yu Chenxia
Publication year - 2013
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.201202655
Subject(s) - oxindole , carbene , catalysis , aldehyde , chemistry , isatin , organic chemistry , medicinal chemistry , combinatorial chemistry
Smooth as isatin! A straightforward synthesis of spirocyclic oxindole–dihydropyranones through an N ‐heterocyclic‐carbene‐catalyzed [4+2] annulation of α‐bromo‐α,β‐unsaturated aldehydes or α,β‐dibromoaldehyde bearing γ‐H with isatin derivatives under mild reaction conditions is disclosed (see scheme). The concise construction, ready availability of the starting materials, avoidance of external oxidants, and the potential utilization value of final products in molecular biology and pharmacy makes this approach particularly attractive.