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Ringschlussreaktionen von 1‐(2‐Aminophenyl)‐1‐phenyl‐äthylenen durch Kondensation mit Phosgen
Author(s) -
Künzle F.,
Schmutz J.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530415
Subject(s) - chemistry , phosgene , medicinal chemistry , isocyanate , aluminium chloride , condensation , methylene , chloride , methyl group , propene , aluminium , polymer chemistry , group (periodic table) , organic chemistry , catalysis , polyurethane , physics , thermodynamics
Cyclization of 1‐(2‐aminophenyl)‐1‐phenyl‐ethylenes or 1‐(2‐aminophenyl)‐1‐phenyl‐propenes (II) by condensation with phosgene led to 4‐phenyl‐carbostyrils (III) or 2‐chloro‐4‐phenyl‐quinolines (IV). Similarly, thiophosgene afforded 4‐phenyl‐thiocarbostyril. Treatment of 1‐(2‐aminophenyl)‐2‐methyl‐1‐ p ‐tolyl‐propene (VII) with phosgene led to the corresponding isocyanate IX, which cyclized in the presence of aluminum chloride with loss of a methyl group to 3‐methyl‐4‐ p ‐tolyl‐carbostyril (III‐6). However, 1‐(2‐aminophenyl)‐2‐methyl‐1‐phenyl‐propene (VIII) treated with phosgene gave the isocyanate XI and 3‐phenyl‐3‐isopropenyloxindole (X). Cyclization of the isocyanate XI with aluminium chloride led simultaneously to 3‐methyl‐4‐phenyl‐carbostyril (XIV), and with migration of a methyl group to 3‐methylene‐4‐methyl‐4‐phenyl‐3. 4‐dihydro‐carbostyril (XV).