Sequential Intramolecular Diels–Alder Reaction of 3-Heteroaryl-2-propenylamides of Ethenetricarboxylate
Hirotaka Sugiura
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka, 599-8531 Japan
Search for more papers by this authorCorresponding Author
Shoko Yamazaki
Department of Chemistry, Nara University of Education, Takabatake-cho, Nara, 630-8528 Japan
E-mail: [email protected]Search for more papers by this authorAkiya Ogawa
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka, 599-8531 Japan
Search for more papers by this authorHirotaka Sugiura
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka, 599-8531 Japan
Search for more papers by this authorCorresponding Author
Shoko Yamazaki
Department of Chemistry, Nara University of Education, Takabatake-cho, Nara, 630-8528 Japan
E-mail: [email protected]Search for more papers by this authorAkiya Ogawa
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka, 599-8531 Japan
Search for more papers by this authorAbstract
The reaction of 1,1,2-ethenetricarboxylic acid 1,1-diethyl ester with E-3-(2-furyl)-2-propenylamines under the amide condensation conditions (EDCI/HOBt/Et3N) on heating at 80–110°C afforded cis-fused tricyclic compounds, furo[2,3-f]isoindoles as major product. On the other hand, the reaction with E-3-(3-furyl)-2-propenylamines afforded trans-fused tricyclic compounds predominantly. The formation of amide/[4 + 2] cycloaddition/hydrogen-shift reactions proceed sequentially. The observed stereoselectivity of the fused rings has been investigated by the density functional theory calculations. The reaction of 1,1,2-ethenetricarboxylic acid 1,1-diethyl ester with 3-(3-pyridinyl)-2-propen-1-amine under the amide condensation conditions afforded HOBt-incorporated 3,4-trans-pyrrolidine selectively. The chemoselectivity and stereoselectivity of the reactions with (3-heteroaryl)-2-propen-1-amines depend on the nature of heteroarenes.
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