70474-52-1

Upstream product

• 4664-08-8 cinchomeronic anhydride 
• 5444-01-9 3-cyano-4-methylpyridine 
• 3222-50-2 4-methylnicotinic acid 
• 70474-45-2 (6,7-Dimethoxy-1-methylene-3,4-dihydro-1H-isoquinolin-2-yl)-pyridin-3-yl-methanone 
• 98-88-4 benzoyl chloride 

Downstream Products

• 127819-75-4 3-(4,5-Dimethoxy-2-ethylphenyl)-2,7-naphthyridin-1(2H)-one 
• 127819-74-3 3-(4,5-Dimethoxy-2-vinylphenyl)-2,7-naphthyridin-1(2H)-one 

Relevant academic research and scientific papers

Simultaneous formation of 8H-isoquino[2,1-b][2,7]naphthyridin-8-ones and 13H-pyrido[4',3':3,4]pyrrolo[2,1-b][3]benzazepin-13-ones, a novel potential alkaloidal system

Condensation of 3,4-dihydro-6,7-dimethoxyisoquinoline (4) with 4-methylnicotinoyl chloride (12) in refluxing pyridine gives 5,6,13,13a-tetrahydro-2,3-dimethoxy-8H-isoquino[2,1-b][2,7]naphthyridi n-8-one (11), along with some of its 13,13a-didehydro derivative 7. A similar reaction of 4 with 4-(chloromethyl)nicotinoyl chloride (14) affords, in addition to 7, the isomeric product 10,11-dihydro-7,8-dimethoxy-13H-pyrido[4',3':3,4]pyrrolo[2,1-b][3]benz azepin-13-one (3). Analogous pairs of products are obtained from 3,4-dihydro-6,7-(methylenedioxy)- and 3,4-dihydro-6,7,8-trimethoxy-isoquinolines (15 and 18, resp). The structure of 3 was established by extensive NMR data and confirmed by single-crystal X-ray studies. Structure 7 has the ring system of the Alangium alkaloids like alangimarine (1), while the isomeric ring system 3 is predicted to be present in nature on biogenetic reasoning.

Aza analogues of protoberberine and phtalideisoquinoline alkaloids

Anions derived from furopyridin-3(1H)-one, by treatment with lithium diisopropylamide, react with substituted, 3,4-dihydroisoquinolines and 2-methyl-3,4-dihydroisoquinolinium salts yielding nitrogen analogues of protoberberine and phtalideisoquinoline alkaloids, respectively.

Activated Imines as Carbon Electrophiles: Applications in Alkaloid Synthesis

3,4-Dihydroisoquinolines and 3,4-dihydro-β-carbolines react with trimethylsilyl trifluoromethanesulphonate to form complexes that react readily with the lithio derivatives of 3-cyano-4-methylpyridines; the method has been applied to the synthesis of the Alangium alkaloids, (+/-)-alangimaridine and alangimarine.

CYCLIZATION REACTION OF 1-METHYLENE-1-NICOTINOYL-1,2,3,4-TETRAHYDROISOQUINOLINES AND A TOTAL SYNTHESIS OF ALAMARINE

Under photochemical, thermal and acylating conditions cyclization of 1-methylene-2-nicotinoyltetrahydroisoquinolines was investigated and as a result the alkaloid alamarine was synthesized via the route involving enamide cyclization under both termal and photochemical conditions.