Reactions of indoles with ortho esters, N,N‐dimethylformamide and N,N‐dimethylacetamide dialkyl acetals | Zendy

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Reactions of indoles with ortho esters, N,N‐dimethylformamide and N,N‐dimethylacetamide dialkyl acetals

Author(s) -

Bergman Jan

Publication year - 1985

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570220223

Subject(s) - chemistry , dimethylacetamide , indole test , carbocation , yield (engineering) , medicinal chemistry , methane , dimethylformamide , acetal , alkyl , organic chemistry , solvent , materials science , metallurgy

Indole and N ‐methylindole react with oxa stabilized carbocations generated in situ from orthoformates to yield tris(3‐indolyl)methane. The unsymmetrical isomers, e.g. 2‐( N ‐methyl‐3‐indolyl)di( N ‐methyl‐3‐indolyl)‐methane ( 4 ), were not formed as established by an independent synthesis. N,N ‐Dimethylacetamide dimethyl‐acetal reacted with 2‐alkyl substituted indoles to produce 1,1‐bis(3‐indolyl)ethanes ( 3 ).

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