The eyntheeia of tetrehydroprotoberberine~' by the reaction of l-benzyl-1,2,3,4-tetrahydroisoquinolinee with formaldehyde by a Pictet-Spengler type reaction' is well documented and provides few,surprises. However, we wish to report on the unueual bchaviour of l-(2-bromo-4,5-methylenedioxy-a-methyl)
Enamide photochemistry. The elimination of ortho-substituents in the photocyclization of 2-aroyl-6,7-dimethoxy-1-methylene-1,2,3,4-tetrahydroisoquinolines
β Scribed by George R. Lenz
- Publisher
- Elsevier Science
- Year
- 1973
- Tongue
- French
- Weight
- 195 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
We have reinvestigated the anodic oxidation of 1,4~hydro-6.7-d;methoxy-4-(3.4-dimethoxy~l)-2-me~y~~u~o~-3(2H)~ne and found it to yield a new product 2.3.7.9-tetramethoxy-ll-(N-methylscetamido)i~[~,e]~cloh~~m-5~e. In order to investigate reactions of this rype 2-acyl-6.7-~imethoxy-4\_(3,4-dimethoxy~l
Basic treatment In methanol of linearly condensed 1,3-benzothiazinedichloro-&lactam 1 led to a 1,4-benzothiazepi 2, a tetraaubetituted isoquinoline 2, and a thiazole &sulfide derivative 4 via a new ring transformation. The structure of the thiazola disulfide 4 was determined by X-ray diffraotion.
In the preceding cosxnunication,l we noted that the ozonoly~is of 6,7-dimethoxy-exo--tricyclcf3.2.1.02'4]oct-6-ene (1) in methanol gave 7,7-dimethoxy-z-tricycq3.2.1.02'~act-6-one (2), in addition to the expected osonolysis product 3. We now wieh to report -our mechanistic studies related to this eno