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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.