SELECTIVE N-FUNCTIONALIZATION OF 6-SUBSTITUTED-2-PYRIDONES

被引：99

作者：

LIU, H ^{[1
]}

KO, SB ^{[1
]}

JOSIEN, H ^{[1
]}

CURRAN, DP ^{[1
]}

机构：

[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 49期

基金：

美国国家卫生研究院;

关键词：

2-PYRIDONE; N-ALKYLATION; N-PROPARGYLATION;

D O I：

10.1016/0040-4039(95)01917-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6-Substituted-2-pyridones can be selectively N-alkylated by treatment with NaH/LiBr in a mixture of DMF and DME. Yields of N-propargylated, N-allylated, and other N-functionalized products are good, and only small amounts of the isomeric O-alkylated product (<10%) are typically formed.

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收藏

页码：8917 / 8920

页数：4

相关论文

共 15 条

[1] A 10-STEP, ASYMMETRIC-SYNTHESIS OF (S)-CAMPTOTHECIN [J].

COMINS, DL ;

BAEVSKY, MF ;

HONG, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10971-10972

[2] ASYMMETRIC-SYNTHESIS OF CAMPTOTHECIN ALKALOIDS - A 9-STEP SYNTHESIS OF (S)-CAMPTOTHECIN [J].

COMINS, DL ;

HONG, H ;

JIANHUA, G .

TETRAHEDRON LETTERS, 1994, 35 (30) :5331-5334

[3] N-ALKYLATION VS O-ALKYLATION IN THE MITSUNOBU REACTION OF 2-PYRIDONE [J].

COMINS, DL ;

GAO, JH .

TETRAHEDRON LETTERS, 1994, 35 (18) :2819-2822

[4] NEW 4+1 RADICAL ANNULATIONS - A FORMAL TOTAL SYNTHESIS OF (+/-)-CAMPTOTHECIN [J].

CURRAN, DP ;

LIU, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5863-5864

[5]

CURRAN DP, IN PRESS ANG CHEM IN

[6]

DIEZBARRA AE, 1994, SYNTHETIC COMMUN, V24, P1057

[7] CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF 20(S)-CAMPTOTHECIN - A PRACTICAL APPLICATION OF THE SHARPLESS ASYMMETRIC DIHYDROXYLATION REACTION [J].

FANG, FG ;

XIE, SP ;

LOWERY, MW .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6142-6143

[8] ENANTIOSELECTIVE SYNTHESIS OF 20(S)-CAMPTOTHECIN USING SHARPLESS CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

JEW, SS ;

OK, KD ;

KIM, HJ ;

KIM, MG ;

KIM, JM ;

HAH, JM ;

CHO, YS .

TETRAHEDRON-ASYMMETRY, 1995, 6 (06) :1245-1248

[9]

JOSIEN H, UNPUB

[10]

POTMESIL M, 1995, CAMPTOTHECINS NEW AN