Synthesis of phenaleno[1,9‐ bc ]thiophene | Zendy

Tominaga Yoshinori | Zendy; Lee Milton L. | Zendy; Castle Raymond N. | Zendy

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Synthesis of phenaleno[1,9‐ bc ]thiophene

Author(s) -

Tominaga Yoshinori,

Lee Milton L.,

Castle Raymond N.

Publication year - 1981

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.5570180526

Subject(s) - thiophene , chemistry , yield (engineering) , potassium hydroxide , sodium hydroxide , halogenation , acetone , medicinal chemistry , aldehyde , organic chemistry , sodium cyanide , nuclear chemistry , cyanide , catalysis , materials science , metallurgy

The cyclization of 2‐acetonylthionaphthalene, prepared from 2‐mercaptonaphthalene (1) and chloro‐acetone in the presence of sodium hydroxide, with polyphosphoric acid gave 1‐methylnaphtho[2,1‐ b ]thiophene (4) in 64% overall yield from 1. By bromination with N ‐bromosuccinimide, 4 was converted in 40% yield into l‐bromomethylnaphtho[2,1‐ b ]thiophene (8) . Treatment of 8 with potassium cyanide in a phase‐transfer medium gave l‐cyanomethylnaphtho[2,1‐ b ]thiophene (10) in good yield. Compound 10 was reduced to the corresponding aldehyde 11 and then cyclized with polyphosphoric acid to phenaleno[l,9‐ bc ]thiophene (12) in 24% overall yield from 10.

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