Synthesis and stereochemistry of new naphth[1,3]oxazino[3,2-a]benzazepine and naphth[1,3]oxazino[3,2-e]thienopyridine derivatives

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• 作者：Petra Barta^a ; Istvá ; n Szatmá ; ri^a ; Ferenc Fü ; lö ; p^a ; ^{fulop@pharm.u-szeged.hu" class="auth_mail" title="E-mail the corresponding author} ; Matthias Heydenreich^b ; Andreas Koch^b ; Erich Kleinpeter^b ; ^{ekleinp@uni-potsdam.de" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Modified Mannich reaction ; Thienopyridine ; Benzazepine ; NMR spectroscopy ; Stereochemistry ; Theoretical calculations
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：12 May 2016
• 年：2016
• 卷：72
• 期：19
• 页码：2402-2410
• 全文大小：1062 K

文摘

Through the reactions of 1- or 2-naphthol and 4,5-dihydro-3H-benz[c]azepine or 6,7-dihydrothieno[3,2-c]pyridine, new aminonaphthol derivatives were prepared. The syntheses were extended by using N-containing naphthol analogues such as 5-hydroxyisoquinoline and 6-hydroxyquinoline. The ring closures of the novel bifunctional compounds were also achieved, resulting in new naphth[2,1-e][1,3]oxazines, naphth[1,2-e][1,3]oxazines, isoquinolino[5,6-e][1,3]oxazines and quinolino[5,6-e][1,3]oxazines. ¹H NMR spectra of the target heterocycles 16, 20 and 21 were sufficiently resolved to indentify the present stereochemistry; therefore, beside computed structures, spatial experimental (dipolar coupling–NOE) and computed (ring current effect of the naphthyl moiety–TSNMRS) NMR studies were employed. The studied heterocycles exist exclusively as S(14b),R(N), R(14b),S(N), and S(16b)S(N) isomers, respectively. The flexible moieties of the studied compounds prefer.