The Conjugate Addition of Benzoyl(thioacetanilides) to Nitroalkenes Synthesis of Functionalized Thiophenes and Pyrroles | Zendy

BogdanowiczSzwed Krystyna | Zendy; Palasz Aleksandra | Zendy; Rys Barbara | Zendy; Soja Dorota | Zendy; Grochonski Jacek | Zendy; Serda Pawer | Zendy

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The Conjugate Addition of Benzoyl(thioacetanilides) to Nitroalkenes Synthesis of Functionalized Thiophenes and Pyrroles

Author(s) -

BogdanowiczSzwed Krystyna,

Palasz Aleksandra,

Rys Barbara,

Soja Dorota,

Grochonski Jacek,

Serda Pawer

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619960918

Subject(s) - chemistry , acetic anhydride , aryl , hydrolysis , benzoyl chloride , benzoyl peroxide , yield (engineering) , dehydration , hydrochloric acid , medicinal chemistry , organic chemistry , oxime , conjugate , ring (chemistry) , catalysis , mathematics , alkyl , polymer , materials science , metallurgy , polymerization , biochemistry , mathematical analysis

Reaction of benzoyl(thioacetanilides) 1 with ( E )‐β‐nitrostyrenes 2 yields 4‐aryl‐2‐arylimino‐3‐benzoyl‐5‐hydroxyimino‐2,3,4,5‐tetrahydrothiophenes 7 . In PPA medium the oxime function of 7 undergoes dehydration and hydrolysis leading to 4‐aryl‐2‐arylimino‐3‐benzoyl‐2,5‐dihydro‐5‐oxothiophenes 9 . Reaction of 7 with hydrochloric acid involves dehydration, hydrolysis and ring transformation to 1,4‐diaryl‐3‐benzoyl‐2,5‐dihydro‐5‐oxo‐2‐thioxopyrroles 10 . Acetic anhydride reacts with 7 to yield 5‐acetylimino‐4‐aryl‐2‐arylimino‐3‐benzoyl‐2,5‐dihydrothiophenes 11 .

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