A Microwave-Assisted Alternative Synthesis of 8-Amino-2-methyl-3,4-dihydroisoquinoli­n-1-one

Abstract

A shorter, alternative synthesis of 8-amino-2-methyl-3,4-dihydroisoquinolin-1-one is described in 32% overall yield, over three steps starting from commercially available 2-methyl-6-nitrobenzonitrile. The synthesis includes two 'one-pot' procedures in which the key process involves the microwave-assisted hydrolysis of a nitrile group followed by lactamization under elevated temperatures.

Photocycloaddition and Rearrangement Reactions in a Putative Route to the Skeleton of Plicamine-Type Alkaloids

“…To this end, lactams 7a,b were N-methylated (Scheme 7) under standard conditions. 20 The resulting products 18 were converted into cyclobutanones 19, which in turn were submitted to the Tamura conditions of the Beckmann rearrangement. Disappointingly, the only isolable products in both cases were the undesired rearrangement products 20.…”

Total Synthesis of Waltherione F, a Nonrutaceous 3-Methoxy-4-quinolone, Isolated from Waltheria indica L. F.

“…Our synthetic efforts began with oxidation of the anisole 9 with KMnO 4 in H 2 O (Scheme ); this gave the benzoic acid 10 in 67% yield . Taking into account that the proposed strategy heavily relies on a final selective O -methylation of a tridentate substrate, and that this is a challenging task, a simple model was first built, implementing an approach analogous to that of Hradil et al…”