1,7-Sigmatropic rearrangement in 1,2-dihydro and 1,2,3,4-tetrahydroquinoline synthesis using marine sponge/H₂C₂O₄ as a catalyst

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• 作者：Mohammad Reza Shushizadeh^a ; ^{m.r.shushizadeh@gmail.com" class="auth_mail" title="E-mail the corresponding author} ; Azar Mostoufi^a ; Abdol-azim Behfar^a ; Minoo Heidary^b
• 关键词：Tetrahydroquinoline ; 1 ; 7-Sigmatropic rearrangement ; Chirality ; Imino Diels&ndash ; Alder ; Marine sponge/oxalic acid
• 刊名：Arabian Journal of Chemistry
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：8
• 期：6
• 页码：868-872
• 全文大小：1697 K

文摘

Marine sponge/oxalic acid was found to be an efficient catalyst for the imino Diels–Alder reaction of synthesized N-aryl-substituted aldimines and various alkenes to provide 1,2-dihyro and 1,2,3,4-tetrahydro-quinolines using 1,7-sigmatropic rearrangement with induction of chirality. Mild reaction conditions, simple experimental procedure, good yields of products, and optical active induction render this new method attractive for 1,7-sigmatropic rearrangement of imino Diels–Alder reaction.