Benzo[ b ]thiophene derivatives. XXV. Condensation and reductive alkylation of 3‐aminoalkylbenzo[ b ]thiophenes with formaldehyde | Zendy

Campaigne E. | Zendy; Homfeld E. | Zendy

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Benzo[ b ]thiophene derivatives. XXV. Condensation and reductive alkylation of 3‐aminoalkylbenzo[ b ]thiophenes with formaldehyde

Author(s) -

Campaigne E.,

Homfeld E.

Publication year - 1979

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.5570160706

Subject(s) - chemistry , thiophene , formaldehyde , alkylation , formic acid , pyridine , medicinal chemistry , organic chemistry , condensation , condensation reaction , catalysis , physics , thermodynamics

The reductive alkylation of 3‐aminomethylbenzo[ b ]thiophene by the Eschweiler‐Clarke (formaldehyde‐formic acid) method and of 3‐β‐aminoethylbenzo[ b ]thiophene by the Borch (formaldehyde‐cyanoborohydride) method proceeded in good yields. However, the Eschweiler‐Clarke reaction with 3‐β‐aminoethylbenzo[ b ]thiophene gave the Pictet‐Spengler cyclized product, N ‐methyl‐1,2,3,4‐tetrahydrobenzo[ b ]thieno[2,3 c ]pyridine. Mechanistic aspects of the latter reaction were investigated.

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