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Nucleophilic‐Bisphosphine‐Catalysed One‐Pot Sequential [4+2]/[4+2] Annulation of an Allenoate with Benzylidenepyrazolones
Author(s) -
Jia Yu,
Tang Xiao,
Cai Guowei,
Jia Ruxuan,
Wang Boran,
Miao Zhiwei
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500399
Subject(s) - annulation , chemistry , nucleophile , catalysis , pyrazole , butane , naphthalene , medicinal chemistry , organic chemistry , combinatorial chemistry
An efficient bisphosphine‐catalysed sequential [4+2]/[4+2] annulation reaction of a γ‐benzyl allenoate with benzylidenepyrazolones has been developed. Under the catalysis of DPPB [1,3‐bis(diphenylphosphanyl)butane], the [4+2]/[4+2] annulation proceeded smoothly to give spiro‐pyrazolidinone derivatives in moderate yields. This protocol provides a simple and practical strategy for the construction of highly substituted 2 H ‐spiro[naphthalene‐pyrazole] skeletons.