Cycloaddition of the iminoketene 6, derived from anthranilic acid (7), with 3,4-dihydro-6,7-dimethoxyisoquinoline ( 16), followed by dehydrogenation, gave 7,8-dihydro-2,3-dimethoxy-8-oxoisoquinolo[ 1,2-6]quinazoline (23), which was also obtained from papaverine (21) or 6,7-dimethoxyisoquinoline (20), Moreover, this paper reports a total synthesis of evodiamine (1) and rutecarpine (3), Recently, a systematic method available for the synthesis of complicated compounds has been discussed3 and Corey has developed a computer-assisted synthetic analysis, which al-
Treatment of the sulphinamide anhydride 1 -methyl-3.2.1 -benzoxathiazin-4(1 /+)-one S-oxide (5). derived from N-methylanthranilic acid (1). with amides ( 9)-( 11) gaveglycorine (1 4),glomerine ( 1 5). and homoglomertne (1 6), respectively Reaction of the N-unsubstituted sulphinamide anhydride (6) with O-benzyl-lactamide (1 3), followed by debenzylation of the resulting 2-(1 -benzyloxyethyl)quinazolin-4(3H) -one (1 7) yielded crysogine (1 8) Condensation of the sulphinamide anhydrides ( 7) and (8), prepared from the corresponding dimethoxy-and methylenedioxy-anthranilic acid derivatives (3) and (4). with 3.4-dihydro-(3-carboline (1 9) furnished euxylophoricines A (20) and C (21). 5.1 1 -Dimethyldibenzo[b,f] [1,5]diazoc1ne-6.12(5H.1 1H)-dione ( 22) was obtained from the N-methylsulphinamide anhydride (5).
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