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Synthesis of 5,6‐Dihydropyrazolo[5,1‐ a ]isoquinoline and Ethyl ( Z )‐3‐Acetoxy‐3‐tosylpent‐4‐enoate through Tertiary‐Amine‐Catalyzed [3+2] Annulation
Author(s) -
Lei Yu,
Xing JiaoJiao,
Xu Qin,
Shi Min
Publication year - 2016
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.201600577
Subject(s) - annulation , chemistry , isoquinoline , dabco , octane , catalysis , amine gas treating , organic chemistry , medicinal chemistry , stereochemistry
The 1,4‐diazabicyclo[2.2.2]octane (DABCO) catalyzed divergent [3+2] annulation of C,N‐cyclic azomethine imines with δ‐acetoxyallenoates was developed; 5,6‐dihydropyrazolo[5,1‐ a ]isoquinolines and ethyl ( Z )‐3‐acetoxy‐3‐tosylpent‐4‐enoates were afforded in moderate to good yields in a one‐pot manner under mild conditions. This annulation reaction provides a highly efficient method to construct dinitrogen‐fused heterocycles and ethyl ( Z )‐3‐acetoxy‐3‐tosylpent‐4‐enoates at the same time.