Tetrahedron p. 1063 - 1072 (1994)
Update date:2022-08-03
Topics:
Kuroki
Kuroki, Yoshiaki
Akao
Akao, Ryosuke
Inazumi
Inazumi, Tomonori
Noguchi
Noguchi, Michihiko
Intramolecular ene reaction of 4-(2-alkenylamino)-3-formyl-2(2H)- chromenones 7 involving carbonyl enophile proceeded stereoselectively to afford 5-hydroxychromen[3,4-b]-azepines 14. The intramolecular nucleophilic attack of hydroxy group to the enemine moiety in 14 gave 1,2-dihydro-2,4- ethanochromen[4,3-d][1,3]oxazin-5(4H,5H)-one derivatives 13 as final products. PM3 MO calculations of the process reveal that this ene reaction proceeds with two steps through an intermediate.
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