66216-58-8

Upstream product

• 60394-91-4 2-(4,5-dimethoxy-2-hydroxyphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene 
• 51931-01-2 N-phenyl-N,N,N-trimethylammmonium 4-methylbenzenesulfonate 
• 180411-17-0 2-bromo-6,7-methylenedioxy-1-naphthylamine 
• 180411-11-4 6-bromonaphtho[2,3-d][1,3]dioxol-5-ol 
• 180411-09-0 6,6-dibromo-7,8-dihydro-6H-naphtho[2,3-d][1,3]dioxol-5-one 
• 180411-19-2 N-(6-Bromo-naphtho[2,3-d][1,3]dioxol-5-yl)-formamide 
• 213698-51-2 N-(6-bromonaphtho[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-2-methylpropionamide 
• 180411-13-6 2-(6-bromo-naphtho[2,3-d][1,3]dioxol-5-yloxy)-2-methylpropionamide 
• 95689-09-1 cis-N-methyl-6,7-methylenedioxy-2-(2,4,5-trimethoxy)-1,2,3,4-tetrahydro-1-naphthylamine 
• 88775-70-6 6,7-methylenedioxy-2-(2,4,5-trimethoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one 
• 41303-45-1 6,7-methylenedioxy-1-tetralone 
• 213698-57-8 N-[6-(2,4,5-Trimethoxy-phenyl)-naphtho[2,3-d][1,3]dioxol-5-yl]-formamide 
• 74-88-4 methyl iodide 
• 95688-78-1 cis-6,7-methylenedioxy-1-(N-methylformamido)-2-(2,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

A versatile synthesis of fully aromatic benzo[c]phenanthridine alkaloids

A versatile new approach for the synthesis of benzo[c]phenanthridine alkaloids is described and is illustrated by the preparation of eight different alkaloids. The key steps are Smiles rearrangements, which allow easy access to 2-bromo-1-naphthylamines from 2-bromo-1-naphthols, and the attachment of the D-ring unit by Suzuki coupling.

Conversion of the Naturally Occurring Amide Alkaloids into O5 Benzophenanthridinium Alkaloids. A New Synthetic Sequence to Antitumour Benzophenanthridine Alkaloids

Cyclisation of methyl integriamide (17a) and methyl isoarnottianamide (17b) by the Bischler-Napieralski reaction gave the naturally occurring O5 benzophenanthridine alkaloids, chelirubine (5a), and chelilutine (5b), respectively; this was extended to give a generally applicable, versatile synthesis of benzophenanthridine alkaloids from 2-aryl-3,4-dihydronaphthalen-1(2H)-ones (13).Treatment of the tetralones (13) with methylamine and titanium tetrachloride followed by sodium borohydride provided the cis-2-aryl-N-methyl-1,2,3,4-tetrahydro-1-naphthylamines (14) which were converted into the N-formyl derivatives (15) with freshly prepared chloral in good yields.Dehydrogenation of the resulting formamides (15) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) gave the fully aromatised amines corresponding to methyl integriamide (17a).Bischler-Napieralski reaction of these amides (17) furnished the desired quaternary benzophenanthridine alkaloids (5).