REGIOSELECTIVE SYNTHESIS OF 6-ALKYLATED LUMAZINE DERIVATIVES

被引:13
作者
IGARASHI, M
TADA, M
机构
[1] Department of Chemistry, School of Science and Engineering, Waseda University, Tokyo, 169, Shinjuku-ku
关键词
D O I
10.1002/jhet.5570320320
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regiospecific synthesis of alkylated lumazines is achieved by hetero Diels-Alder addition between an oxadiazinone 2 and enamine. The reactions proceed stepwise by cycloaddition, decarboxylation and deamination to produce the 6-alkylated lumazines.
引用
收藏
页码:807 / 810
页数:4
相关论文
共 21 条
[1]   DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].
AFARINKIA, K ;
VINADER, V ;
NELSON, TD ;
POSNER, GH .
TETRAHEDRON, 1992, 48 (42) :9111-9171
[2]   REACTIONS OF 1,3-DIMETHYL-5,6-DIAMINOURACIL [J].
BLICKE, FF ;
GODT, HC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (10) :2798-2800
[3]  
BROWN DJ, 1988, CHEM HETEROCYCLIC CO, V24, P511
[4]  
DEWER MJS, 1977, J AM CHEM SOC, V99, P4899
[5]   PTERIDINE DERIVATIVES .2. METHYLATION OF 2-4-DIHYDROXY-6 AND 7-PHENYLPTERIDINE, AND RELATED TOPICS [J].
DICK, GPG ;
WOOD, HCS ;
LOGAN, WR .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (JUL) :2131-2136
[6]  
EGUCHI T, MOPAC VER 6 02 MS DO
[7]   SYNTHESIS OF UNSYMMETRICAL PYRAZINES BY REACTION OF AN OXADIAZINONE WITH ENAMINES [J].
GANESAN, A ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :6155-6157
[8]   REACTIVITY OF 3H-PYRIMIDO[5,4-C][1,2,5]OXADIAZIN-3-ONE TOWARDS CARBANIONS - SYNTHESIS OF PTERIDINE-2,4-DIONES [J].
GIORI, P ;
POLI, T ;
VERONESE, AC ;
VICENTINI, CB ;
MANFRINI, M ;
GUARNERI, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (06) :1661-1665
[9]   PTERIDINE .82. SYNTHESIS AND REACTIVITY OF LUMAZINE-7-SULFENIC ACIDS [J].
HECKEL, A ;
PFLEIDERER, W .
HELVETICA CHIMICA ACTA, 1986, 69 (05) :1095-1106
[10]   HYDROBORATION AND REDUCTION OF ENAMINES .3. REACTION OF EXO-ENAMINES AND ENDO-ENAMINES WITH DIBORANE AND SODIUM-BOROHYDRIDE [J].
KUDO, T ;
NOSE, A .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1974, 94 (11) :1475-1483