550358-40-2Relevant articles and documents
Preparation method of aporphine alkaloid
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Paragraph 0055; 0062; 0064; 0112-0113; 0116-0117; 0120-0121, (2021/06/09)
The invention discloses a preparation method of aporphine alkaloid as shown in a formula III. The method comprises the following steps: taking a benzaldehyde compound as shown in a formula III-0 as a raw material, and sequentially carrying out Wittig reaction, Pictet-Spengler reaction, Heck reaction and palladium carbon hydrogen deprotection. A bromine-containing benzaldehyde derivative is selected as a raw material, the carbon-carbon coupling co-production rate and the reaction rate are increased through bromine atoms, and the reaction activity is improved; benzyl chloroformate is adopted for NH protection, and an electron withdrawing group is introduced, so that the reaction yield can be improved; and a styrene methyl ether derivative directly reacts with an acylated phenylethylamine derivative in an acid catalysis system by adopting a one-pot method so as to obtain benzyl tetrahydroisoquinoline. The preparation method has the advantages of mild reaction conditions, low toxicity of used reagents, easily available raw materials, convenient post-treatment and simpler reaction route compared with previous reports, and can be suitable for various reaction substrates.
Total synthesis of lennoxamine and chilenine via ring-expansion of isoindoloisoquinoline to isoindolobenzazepine
Koseki, Yuji,Katsura, Shinya,Kusano, Shuichi,Sakata, Harumi,Sato, Hiroto,Monzene, Yoshinori,Nagasaka, Tatsuo
, p. 527 - 540 (2007/10/03)
Convenient synthesis of the benzazepine alkaloids, lennoxamine (1) and chilenine (2), is described. The key steps are conversion of methylenelactam (5) to an N-tertiary acyliminium ion precursor (16) and a novel expansion of the six-membered ring of 4 to a benzazepine ring system (3b), which could be transformed into lennoxamine (1) and chilenine (2).