124293-98-7

Upstream product

• 59444-56-3 1-(2'-bromo-4',5'-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride 
• 59444-59-6 (+/-)-1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 52050-59-6 2,3,9,10-tetramethoxy-8-oxoberbine 
• 6899-65-6 coralydine 
• 308818-03-3 1-[4',5'-dimethoxy-2'-(2-methylbutyryl)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 50461-24-0 (+/-)-1-(3,4-dimethoxybenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline 
• 124293-99-8 4H-6-carbethoxy-1,2,9,10-tetramethoxy-5,6,6a,7-tetrahydrodibenzo[de,g]quinoline 
• 75371-18-5 6,7-Dimethoxy-1,2,3,4-tetrahydroisochinolin-2-carbonsaeure aethylester 

Relevant academic research and scientific papers

Benzolactams. 4. Reaction of 3′,4′- or 4′,5′-Dialkoxy-Substituted 1-(2′-Bromobenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydroisoquinolines with Alkyllithium. 1,2 and 1,4 Additions of Alkyllithium to Benzolactams

Treatment of 1-(2′-bromo-3′,4′-dialkoxybenzyl)-1,2,3,4- tetrahydroisoquinoline carbamates, 1a,c, with excess alkyllithium gave 8-oxoberbines, 2a,c, which were successively attacked in situ with another molecule of alkyllithium to give 1,2 and/or 1,4 addition products. A primary alkyllithium, such as MeLi or BuLi, gave a 1,2 addition product, 8-methyleneberbine 9a or 8-butylideneberbine 3a. t-BuLi preferred 1,4 addition, followed by elimination of the alkoxy group, to give 9-tert-butyl-8-oxoberbine 6a or 7c. s-BuLi gave a mixture of 1,2 and 1,4 addition products, 1-[2′-(2″-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4a and 9-s-butyl-8-oxoberbine 5a. Similar treatments of carbamate 1b having no alkoxy group at its 3′ position gave 1,2 addition products, 8-butylideneberbine 3b, 1-[2′-(2″-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4b, and 1-(2′-pivaloylbenzyl)-1,2,3,4-tetrahydroisoquinoline 6b, in all cases. Reactions of 1a with s-BuMgCl and isoPrMgCl also gave the 1,4 adduct, 5a, and its 9-isoPr analogue, 12a. Treatment of 9a with excess NaBH4 in AcOH gave (±)-coralydine (10b).

PHOTOCHEMICAL SYNTHESIS OF APORPHINES: (+/-)-GLAUCINE, (+/-)-NORGLAUCINE AND (+/-)-DEHYDRONORGLAUCINE

Photochemical cyclization of 3 afforded 5, 4 and 8. 5 on LAH reduction furnished (+/-)-glaucine (6) and on treatment with ethanolic HCl afforded (+/-)-norglaucine (7). 10 obtained by the photocyclization of 9 was converted into 7 and 11 via 12.