TY - JOUR
T1 - Novel intramolecular two-substituent migration accompanying indenoquinolone formation
AU - Staskun, B.
PY - 1972
Y1 - 1972
N2 - Treatment of 2,2,4′-trichloro-2′,5′-dimethylbenzoylacetanilide (2c) with H2SO4 gave 1,5-dichloro-4,6-dimethylindeno[1,2,3-de]quinolin-2(3H)-one (3a) which was identified by spectral (IR) comparison with various isomeric 3. Product 3a may arise via concerted, intramolecular 1,2-shifts of two substituents during cyclization. Substrate 2,2,2′,4′-tetrachloro-3′,5′-dimethylbenzoylacetanilide (2e), in which this rearrangement is not feasible, was converted into 1,4,6-trichloro-5-methyl-7H-dibenz[f, ij]isoquinolin-2(3H)-one (5b).
AB - Treatment of 2,2,4′-trichloro-2′,5′-dimethylbenzoylacetanilide (2c) with H2SO4 gave 1,5-dichloro-4,6-dimethylindeno[1,2,3-de]quinolin-2(3H)-one (3a) which was identified by spectral (IR) comparison with various isomeric 3. Product 3a may arise via concerted, intramolecular 1,2-shifts of two substituents during cyclization. Substrate 2,2,2′,4′-tetrachloro-3′,5′-dimethylbenzoylacetanilide (2e), in which this rearrangement is not feasible, was converted into 1,4,6-trichloro-5-methyl-7H-dibenz[f, ij]isoquinolin-2(3H)-one (5b).
UR - http://www.scopus.com/inward/record.url?scp=29944436602&partnerID=8YFLogxK
U2 - 10.1016/0040-4020(72)88160-2
DO - 10.1016/0040-4020(72)88160-2
M3 - Article
AN - SCOPUS:29944436602
SN - 0040-4020
VL - 28
SP - 5069
EP - 5079
JO - Tetrahedron
JF - Tetrahedron
IS - 19
ER -