Tandem directed lithiations of N-boc-1,2-dihydropyridines toward highly functionalized 2,3-dihydro-4-pyridones

被引：23

作者：

Young, DW ^{[1
]}

Comins, DL ^{[1
]}

机构：

[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 25期

关键词：

D O I：

10.1021/ol052313a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sequential tandem directed lithiations of an N-Boc-4-methoxy-1,2-dihydropyridine have been achieved, leading to C-5,C-6 disubstituted dihydropyridones on acidic workup. The chlorine atom of the dihydropyridone products can in turn be substituted giving rise to diverse substituents at C-6.

引用

页码：5661 / 5664

页数：4

共 26 条

[1]

[Anonymous], 1996, Adv. Nitrogen Heterocycl

[2]

Comins D.L., 1996, COMPREHENSIVE HETERO, V5, P37

[3] Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones [J].

Comins, DL .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (06) :1491-1500

[4] Diels-alder reactions of N-acyl-2-alkyl(aryl)-5-vinyl-2,3-dihydro-4-pyridones [J].

Comins, DL ;

Kuethe, JT ;

Miller, TM ;

Février, FC ;

Brooks, CA .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5221-5234

[5] ALPHA-METALATION OF 1-(TERT-BUTOXYCARBONYL)-1,4-DIHYDROPYRIDINES [J].

COMINS, DL .

TETRAHEDRON LETTERS, 1983, 24 (28) :2807-2810

[6] ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS [J].

COMINS, DL ;

GOEHRING, RR ;

JOSEPH, SP ;

OCONNOR, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2574-2576

[7] ALPHA-METALATION OF 1-(TERT-BUTOXYCARBONYL)-1,2-DIHYDROPYRIDINES [J].

COMINS, DL ;

WEGLARZ, MA ;

OCONNOR, S .

TETRAHEDRON LETTERS, 1988, 29 (15) :1751-1754

[8] Model studies toward the total synthesis of the Lycopodium alkaloid spirolucidine [J].

Comins, DL ;

Williams, AL .

ORGANIC LETTERS, 2001, 3 (20) :3217-3220

[9] PREPARATION OF 1-(TERT-BUTOXYCARBONYL)-2,6-DIALKYL-2,3-DIHYDRO-4-PYRIDONES - A STEREOCONTROLLED SYNTHESIS OF (+/-)-MYRTINE [J].

COMINS, DL ;

LAMUNYON, DH .

TETRAHEDRON LETTERS, 1989, 30 (38) :5053-5056

[10] GRIGNARD ADDITION TO 1-ACYL SALTS OF CHIRAL 4-ALKOXYPYRIDINES - A NEW ENANTIOSELECTIVE PREPARATION OF 2-ALKYL-2,3-DIHYDRO-4-PYRIDONES [J].

COMINS, DL ;

LAMUNYON, DH .

TETRAHEDRON LETTERS, 1994, 35 (40) :7343-7346

← 1 2 3 →