SYNTHESIS AND BIOLOGICAL-ACTIVITY OF NOVEL 1(2H)-FURO[2,3-H]ISOQUINOLINONE, 1(2H)-PYRANO[2,3-H]ISOQUINOLINONE AND 2H-PYRANO[2,3-H]ISOQUINOLINE-1,8-DIONE
Ep. Desouza et Ps. Fernandes, SYNTHESIS AND BIOLOGICAL-ACTIVITY OF NOVEL 1(2H)-FURO[2,3-H]ISOQUINOLINONE, 1(2H)-PYRANO[2,3-H]ISOQUINOLINONE AND 2H-PYRANO[2,3-H]ISOQUINOLINE-1,8-DIONE, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 33(6), 1994, pp. 552-555
A base-catalysed Claisen rearrangement of 7-(2'-bromoallyloxy)-1(2H)-i
soquinolinone (5) and 7-(2'-propynloxy)-1(2H)-isoquinolinone (6) to gi
ve 1(2H)-furo[2,3-h]isoquinolinone (7) and a Claisen rearrangement of
7-(2'-propynyloxy)-1(2H)-isoquinolinone (6) followed by an electrocycl
ic ring closure in N,N-diethylaniline to give 1(2H)-pyrano[2,3-h]isoqu
inolinone (8) are described. Oxidation of compound 8 by 2,3-dichloro-5
,6-dicyanobenzoquinone (DDQ) affords 2H-pyrano[2,3-h]isoquinoline-1,8-
dione (9).