PHOTO-CHEMICAL REACTIONS OF 4-PYRIMIDONES - STRUCTURES AND PROPERTIES OF THE BETA-LACTAMS FORMED

被引:21
作者
HIROKAMI, S
HIRAI, Y
NAGATA, M
机构
[1] TOYAMA MED & PHARMACEUT UNIV,CHEM LAB,SUGITANI,TOYAMA 93001,JAPAN
[2] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,SUGITANI,TOYAMA 93001,JAPAN
[3] TANABE SEIYAKU CO LTD,CHEM RES LAB,TODA,SAITAMA 335,JAPAN
关键词
D O I
10.1021/jo01327a008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The photochemistry of substituted 4-pyrimidone derivatives 1, 3, 5, and 6 was studied in alcoholic solution. Upon irradiation, the fused 4-pyrimidones 1 and 2, 3, 6-trialkyl-4-pyrimidone 3 gave (aminoalkylidenel-d-alkoxy-.d-lactams 2 and 4, respectively. On the other hand, the substituted 4-pyrimidones 5 and 6 did not afford any products with properties expected of iV-alkyl-2-azetidinone. The structure of 2a was confirmed by X-ray crystallographic analysis. The geometrical isomerization about the double bond of the d-lactams obtained was also discussed. © 1979, American Chemical Society. All rights reserved.
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页码:2083 / 2087
页数:5
相关论文
共 23 条
[1]  
AHLBRECHT H, 1968, TETRAHEDRON LETT, P4421
[2]  
AHLBRECHT H, 1969, TETRAHEDRON LETT, P439
[3]   STEREOCHEMISTRY OF BETA-LACTAMS DERIVED FROM ALPHA-KETO-GAMMA-LACTAMS BY RING CONTRACTION - X-RAY ANALYSIS AND DIFFERENTIAL BEHAVIOR WITH SHIFT-REAGENTS OF DIFUNCTIONAL BETA-LACTAMS [J].
BENDER, D ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (22) :3208-3213
[4]   INTERNAL PHOTOADDITION REACTIONS OF 2-PYRONE + N-METHYL-2-PYRIDONE - NEW SYNTHETIC APPROACH TO CYCLOBUTADIENE [J].
COREY, EJ ;
STREITH, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (05) :950-&
[5]  
DESELMS RC, 1972, TETRAHEDRON LETT, P3563
[6]   NUCLEAR MAGNETIC RESONANCE STUDIES OF KETO-ENOL EQUILIBRIA .5. ISOMERIZATION IN ALIPHATIC SCHIFF BASES [J].
DUDEK, GO ;
VOLPP, GP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (18) :2697-&
[7]  
Flynn E. H., 1972, CEPHALOSPORINS PENIC
[8]   PREPARATION AND REACTIONS OF "3-OXO-2-AZABICYCLO[2.2.0]HEX-5-ENES AND OF 3-OXO-1.2.4.6-TETRAMETHYL-2.5-DIAZABICYCLO[2.2.0]HEXANE [J].
FURRER, H .
CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (09) :2780-&
[9]  
GLUSHKOV RG, 1961, ZH OBSHCH KHIM+, V31, P189
[10]  
IBERS JA, 1974, INT TABLES XRAY CRYS, V4, P73