Isomerization and ring-closing metathesis for the synthesis of 6-, 7- and 8-membered benzo- and pyrido-fused N,N-, N,O- and N,S-heterocycles

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• 作者：van Otterlo ; Willem A.L. ; Morgans ; Garreth L. ; Khanye ; Setshaba D. ; Aderibigbe ; Blessing A.A. ; et. al.
• 关键词：Isomerization ; Ring-closing metathesis ; Benzo-fused heterocycles ; 1 ; 4-Benzoxazines ; 1 ; 6-Benzodiazocine ; 1 ; 6-Benzoxazocine ; 1 ; 6-Benzothiazocine ; 1 ; 5-Benzothiazepine
• 刊名：Tetrahedron Letters
• 出版年：2004
• 出版时间：December 6, 2004
• 年：2004
• 卷：45
• 期：50
• 页码：9171-9175
• 全文大小：301 K

文摘

An isomerizationaaaring-closing metathesis (RCM) strategy afforded N-substituted 4H-1,4-benzoxazines from the protected N-allyl-2-(allyloxy)anilines. In addition, RCM was used to synthesize the N-substituted, 8-membered benzo-fused heterocycles from the respective diallyl compounds: 1,2,5,6-tetrahydro-1,6-benzodiazocine, 5,6-dihydro-2H-1,6-benzoxazocine, 5,6,9,10-tetrahydropyrido[2,3-b][1,4]diazocine and 5,6-dihydro-2H-1,6-benzothiazocine 1,1-dioxide. The isomerizationaaaRCM approach also afforded the 7-membered ring system, 2,5-dihydro-1,5-benzothiazepine 1,1-dioxide, from the protected N-allyl-2-(allylsulfonyl)aniline. Furthermore, the structure of 1,6-bis[(4-methylphenyl)sulfonyl]-1,2,5,6-tetrahydro-1,6-benzodiazocine was confirmed by a single crystal X-ray determination.