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The Reactions of Electron‐Rich Heterocycles with Derivatives of Orthocarboxylic Acids; VIII. Proton Acid‐Catalyzed Acylation of Indoles by 2‐Alkoxy‐1,3‐dioxolanes
Author(s) -
Akgün Eyüp,
Tunali Mustafa,
Pindur Ulf
Publication year - 1987
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19873200504
Subject(s) - chemistry , alkoxy group , acylation , catalysis , reactivity (psychology) , sulfosalicylic acid , medicinal chemistry , tris , organic chemistry , alkyl , medicine , alternative medicine , pathology , chromatography , biochemistry
In acid‐catalyzed reactions with 3‐unsubstituted indoles 1 , 2‐alkoxy‐1,3‐dioxolanes 2a‐c behave as acyl equivalents. Depending on the substitution patterns of the reaction partners, the 1,3‐dioxolanium ions 3a‐c , generated in situ from the cyclic ortho esters by the action of sulfosalicylic acid, react to form tris‐(3‐indolyl)alkanes 6 and 9 , bis‐(3‐indolyl)ethenes 7 , or 3‐benzoylindoles 8 . Analogous reactivity was observed with related acyclic ortho esters.