The Reactions of Electron‐Rich Heterocycles with Derivatives of Orthocarboxylic Acids; VIII. Proton Acid‐Catalyzed Acylation of Indoles by 2‐Alkoxy‐1,3‐dioxolanes | Zendy

Akgün Eyüp | Zendy; Tunali Mustafa | Zendy; Pindur Ulf | Zendy

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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.

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