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Synthesis of Indolin‐3‐ones and Tetrahydro‐4‐quinolones from α‐Imino Esters
Author(s) -
Shimizu Makoto,
Takao Yuki,
Katsurayama Haruna,
Mizota Isao
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201200174
Subject(s) - chemistry , lithium diisopropylamide , trimethylsilyl , lithium (medication) , combinatorial chemistry , closure (psychology) , organic chemistry , medicinal chemistry , psychology , ion , psychiatry , deprotonation , economics , market economy
Bringing closure : α‐Imino esters that contain alkoxycarbonyl electron‐withdrawing groups at the α‐position of the imines are transformed into indolin‐3‐ones by a reductive cyclization by using bis(trimethylsilyl) aluminum chloride. The synthesis of trisubstituted tetrahydro‐4‐quinolones was also developed by a 1,3‐aza‐Brook rearrangement/Dieckmann condensation of α‐imino esters with the lithium enolate of trimethylsilylacetate. LDA=lithium diisopropylamide; TMS=trimethylsilyl.