Details

Autor(en) / Beteiligte

• Sugiura, Hirotaka
• Yamazaki, Shoko
• Ogawa, Akiya

Titel

Sequential Intramolecular Diels–Alder Reaction of 3‐Heteroaryl‐2‐propenylamides of Ethenetricarboxylate

Ist Teil von

• Journal of heterocyclic chemistry, 2019-09, Vol.56 (9), p.2592-2603

Ort / Verlag

Hoboken: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Quelle

Wiley-Blackwell Journals

Beschreibungen/Notizen

• 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.