A new method for the synthesis of substituted indeno[1,2‐ b ]thiophene with subsequent ring expansion to form substituted thieno[3,2‐ c ]quinoline | Zendy

Castle Lyle W. | Zendy; Elmaaty Tarek Abou | Zendy

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A new method for the synthesis of substituted indeno[1,2‐ b ]thiophene with subsequent ring expansion to form substituted thieno[3,2‐ c ]quinoline

Author(s) -

Castle Lyle W.,

Elmaaty Tarek Abou

Publication year - 2006

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.5570430316

Subject(s) - chemistry , beckmann rearrangement , quinoline , thiophene , ring (chemistry) , reagent , oxime , medicinal chemistry , amine gas treating , organic chemistry

2‐Phenacylindan‐1,3‐dione ( 3 ) was treated with Lawesson's reagent (2,4‐bis(4‐methoxyphenyl)‐1,3‐dithia‐2,4‐diphosphetane‐2,4‐disulfide) to form 2‐phenyl‐4 H ‐indeno[1,2‐ b ]thiophene‐4‐one ( 4 ). Compound 4 was subsequently reacted with hydroxyl amine to form the oxime ( 5 ), which, upon treatment with polyphosphoric acid, underwent ring expansion (Beckmann rearrangement) to give 2‐phenylthieno[3,2‐ c ]quinoline‐4(5 H )one.

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