The 3+2-type cycloaddition reaction of 2-hydroxy-1,4-naphthoquinones with various alkenes or phenylacetylene was mediated by ammonium cerium(IV) nitrate (CAN) to give the corresponding naphtho[2,3-b]furan-4,9-dione and naphtho[1,2-b]furan-4,5-dione derivatives. The reaction of 2-hydroxy-1,4-benzoquinones with alkenes in the presence of CAN similarly proceeded to give benzofuran-4,7-dione and benzofuran-4,5-dione derivatives. 3-Hydroxy-1H-phenalen-1-one also underwent the CAN-mediated cycloaddition with alkenes or phenylacetylene to give the corresponding 7H-phenaleno[1,2-b]furan-7-one derivatives.
2-羟基-1,4-萘醌与各种烯烃或
苯乙炔在
硝酸铈铵(CAN)的催化下发生3+2型环加成反应,生成相应的
萘并[2,3-b]
呋喃-4,9-二酮和
萘并[1,2-b]
呋喃-4,5-二酮衍
生物。2-羟基-1,4-苯醌与烯烃在CAN存在下同样发生反应,得到
苯并呋喃-4,7-二酮和
苯并呋喃-4,5-二酮衍
生物。3-羟基-1H-
菲兰烯-1-酮也能在CAN的催化下与烯烃或
苯乙炔发生环加成反应,生成相应的7H-
菲兰诺[1,2-b]
呋喃-7-酮衍
生物。