TY - JOUR
T1 - Synthesis of the first [1,3]benzoxazino[3,2-b][1,2]benzoxazine and its tandem retro-Diels-Alder - Diels-Alder rearrangement to a novel [1,3]benzoxazino[2,3-b][1,3]benzoxazine
AU - Goldschmidt, Zeev
AU - Levinger, Shlomo
AU - Gottlieb, Hugo E.
PY - 1994/9/26
Y1 - 1994/9/26
N2 - Thermolysis of 3-methyl-4H-1,2-benzoxazine gave the tetracyclic 12a-methyl-7H,12aH,13H-[1,3]benzoxazino[3,2-b][1,2]benzoxazine, which further rearranged to the isomeric 5a-methyl-5aH,11H,13H-[1,3]benzoxazino[2,3-b][1,3]benzoxazine. Thermolysis of the benzoxazinobenzoxazines gave 2-methyl-4H-1,3-benzoxazine, and o-quinone methide which was trapped by ethyl vinyl ether to give 2-ethoxy-dihydrobenzopyran.
AB - Thermolysis of 3-methyl-4H-1,2-benzoxazine gave the tetracyclic 12a-methyl-7H,12aH,13H-[1,3]benzoxazino[3,2-b][1,2]benzoxazine, which further rearranged to the isomeric 5a-methyl-5aH,11H,13H-[1,3]benzoxazino[2,3-b][1,3]benzoxazine. Thermolysis of the benzoxazinobenzoxazines gave 2-methyl-4H-1,3-benzoxazine, and o-quinone methide which was trapped by ethyl vinyl ether to give 2-ethoxy-dihydrobenzopyran.
UR - http://www.scopus.com/inward/record.url?scp=0027991962&partnerID=8YFLogxK
U2 - 10.1016/0040-4039(94)85380-0
DO - 10.1016/0040-4039(94)85380-0
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AN - SCOPUS:0027991962
SN - 0040-4039
VL - 35
SP - 7273
EP - 7276
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 39
ER -