Tr. Kasturi et S. Arumugam, POTASSAMIDE INDUCED IN-SITU ALKYLATION OF 5,6-DIHYDROISOQUINOLINE WITH ALLYL BROMIDE AND MICHAEL ACCEPTORS, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 35(5), 1996, pp. 468-470
Potassamide induced in situ alkylation of 4-cyano-3-methoxy-1-methyl-5
, 6-dihydroisoquinoline (1a) with allyl bromide gives the 5-allyl- and
5,9-diallyl-5,6-dihydroisoquinolines (1c and 1d), isoquinoline deriva
tive 2 and 4-allyl-1, 2, 3, 4-tetrahydroisoquinolin-3(2H)-one (3a). Ho
wever, potassamide induced in situ alkylation of In with buten-2-one,
mesityl oxide and acrylonitrile results in the formation of only 5-alk
ylated 5,6-dihydroisoquinoline derivatives 1e-g along with fully aroma
tised compound 2.