INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION OF JUXTAPOSED 4-PYRIDONE MOIETIES

被引：19

作者：

JOHNSON, BL ^{[1
]}

KITAHARA, Y ^{[1
]}

WEAKLEY, TJR ^{[1
]}

KEANA, JFW ^{[1
]}

机构：

[1] UNIV OREGON,DEPT CHEM,EUGENE,OR 97403

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(00)73880-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Refluxing 4-hydroxypyridine and alpha,alpha'-dibromo-o-xylene in an ethanolic sodium ethoxide solution affords alpha,alpha'-di(4-pyridon-1-yl)-o-xylene (1) which undergoes a novel [2+2] photocycloaddition reaction in 3:7 ethanol-ether giving cis,syn,cis-12,13-benzo-1,10-diazatetracyclo[8.4.20(5,15).0(6,16)]hexadeca-2,8-diene-4,7-dione(2). The structure of 2 was determined by x-ray crystallographic analysis.

引用

页码：5555 / 5558

页数：4

共 22 条

[1] AYER WA, 1961, TETRAHEDRON LETT, V18, P648
[2] 1-METHOXYCARBONYL-SUBSTITUTED 2,3-DIHYDROPYRIDIN-4(1H)-ONE (METHYL 1,2,3,4-TETRAHYDRO-4-OXOPYRIDINE-1-CARBOXYLATE) AS CHROMOPHORE FOR PHOTOCHEMICAL [2+2]-CYCLOADDITIONS
GUERRY, P
BLANCO, P
BRODBECK, H
PASTERIS, O
NEIER, R
[J]. HELVETICA CHIMICA ACTA, 1991, 74 (01) : 163 - 178
[3] THE PHOTOCHEMICAL[2+2]CYCLOADDITION TO N-METHOXYCARBONYL-5,6-DIHYDRO-4-PYRIDONE
GUERRY, P
NEIER, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (22) : 1727 - 1728
[4] GUERRY P, 1987, CHIMIA, V41, P341
[5] ULTRAVIOLET-LIGHT REPAIR AND MUTAGENESIS REVISITED
HASELTINE, WA
[J]. CELL, 1983, 33 (01) : 13 - 17
[6] SUBSTITUENT EFFECT ON SELECTIVITY IN PHOTOISOMERIZATION OF 4-PYRONES AND 4-PYRIDONES
ISHIBE, N
YUTAKA, S
MASUI, J
IHDA, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11) : 2144 - 2148
[7] PHOTOISOMERIZATION OF 4-PYRIDONES TO 2-PYRIDONES
ISHIBE, N
MASUI, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) : 1152 - 1158
[8] HEAVY-ATOM EFFECT IN PHOTOISOMERIZATION OF 4-PYRONES AND 4-PYRIDONES
ISHIBE, N
YUTAKA, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11) : 2138 - 2143
[9] PHOTOCHEMICAL REARRANGEMENT OF 4-PYRIDONES
ISHIBE, N
MASUI, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) : 3396 - 3397
[10] INFRARED ABSORPTION OF HETEROAROMATIC AND BENZENOID 6-MEMBERED MONOCYCLIC NUCLEI .10. PYRIDONES AND PYRIDTHIONES
KATRITZKY, AR
JONES, RA
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (JUL): : 2947 - 2953

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