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Regioselective Synthesis of Heterospirocyclic Isobenzofuranones and Medium‐Sized Lactones by Multiple Anion Capture Reactions of 1,3‐Dianions
Author(s) -
Langer Peter,
Döring Manfred,
Görls Helmar
Publication year - 2001
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 - 10.1002/1099-0690(200104)2001:8<1511::aid-ejoc1511>3.0.co;2-d
Subject(s) - chemistry , regioselectivity , benzophenone , oxalic acid , medicinal chemistry , phthalic acid , ion , organic chemistry , catalysis
The multicomponent reaction of 1,3‐dianions with ketones and oxalic acid dichloride or diethylmalonic dichloride afforded six‐ to eight‐membered lactones. Treatment of the dianion of 3‐acetylindole with benzophenone and diethylmalonic dichloride resulted in the formation of a cyclic 1,3,5‐triketooctene. The reaction of 1,3‐dianions with ketones and phthalic dichloride resulted in the formation of heterospirocyclic isobenzofuranones rather than of medium‐sized rings.