Formation of benzocyclobutenes from substituted oxocycloocta-2,8-diene-1,2-dicarboxylates

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• 作者：Jure Bezen&scaron ; ek ; Uro&scaron ; Gro&scaron ; elj ; Marta Po膷kaj ; Jurij Svete ; Branko Stanovnik ; ^{branko.stanovnik@fkkt.uni-lj.si" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Benzocyclobutenes ; Oxabicyclo[3.3.1]non-3-ene-2 ; 3-dicarboxylates ; Oxabicyclo[3 ; 3.1]nonanes ; Microwave assisted reactions ; High pressure hydrogenation
• 刊名：Tetrahedron Letters
• 出版年：2015
• 出版时间：14 October 2015
• 年：2015
• 卷：56
• 期：42
• 页码：5705-5708
• 全文大小：1135 K

文摘

Substituted benzocyclobutenes were isolated from the reaction of substituted oxocycloocta-2,8-diene-1,2-dicarboxylates with DMAD which were themselves formed by the microwave assisted [2+2] cycloaddition of cyclic enaminones to dimethyl acetylenedicarboxylate. The high pressure hydrogenation of (1E,2Z)-dimethyl 3-(dimethylamino)-7-oxocycloocta-2,8-diene-1,2-dicarboxylate gave oxabicyclo[3.3.1]non-3-ene-2,3-dicarboxylates, while use of low pressure hydrogenation resulted in only the carbonyl group being reduced to give the corresponding hydroxyl derivative which was proposed as an intermediate of the oxabicyclo[3.3.1]nonanes formed using high pressure hydrogenation.