32039-37-5

Upstream product

• 47539-89-9 5,6,7-trimethoxy-1-(3',4'-dimethoxybenzyl)3,4-dihydroisoquinoline 
• 54-04-6 mescaline 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 

Downstream Products

• 363134-17-2 1-(3,4-dimethoxy-benzyl)-5,6,7-trimethoxy-3,4-dihydro-isoquinoline 2-oxide 
• 1027195-13-6 2-(2,4-diisopropoxy-5-methoxy-phenyl)-1-(3,4-dimethoxy-phenyl)-7,8,9-trimethoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 149355-75-9 14-(3,4-dimethoxyphenyl)-3-hydroxy-2,10,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4’,3’:4,5]pyrrolo[2,1-a]isoquinolin-6-one 

Relevant academic research and scientific papers

Synthesis of (±)-Glaucine and (±)-Neospirodienone via an One-Pot Bischler-Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent

Condensation of 3,4-dimethoxybenzeneethanamine (3d) and various benzeneacetic acids, i.e., 4a-e, via a practical and efficient one-pot Bischler-Napieralski reaction, followed by NaBH4 reduction, produced a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines, i.e., 5a-e, in satisfactory yields (Scheme 3). Oxidative coupling of the N-acyl and N-methyl derivatives 6a-e of the latter with hypervalent iodine ([IPh(CF 3COO)2]) yielded products with two different skeletons (Scheme 4). The major products from N-acyl derivatives 6a-c were (±)-N-acylneospirodienones 2a-c, while the minor was the 3,4-dihydroisoquinoline 7. (±)-Glaucine (1), however, was the major product starting from N-methyl derivative 6e. Possible reaction mechanisms for the formation of these two types of skeleton are proposed (Scheme 5).

Syntheses of lamellarins I and K by [3+2] cycloaddition of a nitrone to an alkyne

Lamellarins I and K were obtained by a new approach based on the 1,3-dipolar cycloaddition of a nitrone to an alkyne. The key cycloaddition yields an isoxazoline which rearranges to afford the central pyrrole ring.