α-amination of nitrogen heterocycles:: Ring-fused aminals

被引：266

作者：

Zhang, Chen ^{[1
]}

De, Chandra Kanta ^{[1
]}

Mal, Rudrajit ^{[1
]}

Seidel, Daniel ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 02期

关键词：

D O I：

10.1021/ja077473r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aromatic aminoaldehydes react with cyclic amines to produce ring-fused aminals under thermal conditions. This process applied to two-step syntheses of the quinazolinone alkaloids deoxyvasicinone and rutaecarpine.

引用

页码：416 / +

页数：3

共 34 条

[1] X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .29. THE IMINIUM ION ROUTE TO AZOMETHINE YLIDES - REACTION OF CYCLIC SECONDARY-AMINES WITH MONO-FUNCTIONAL AND BI-FUNCTIONAL ALDEHYDES [J].

ARDILL, H ;

FONTAINE, XLR ;

GRIGG, R ;

HENDERSON, D ;

MONTGOMERY, J ;

SRIDHARAN, V ;

SURENDRAKUMAR, S .

TETRAHEDRON, 1990, 46 (18) :6449-6466

[2] X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .28. THE IMINIUM ION ROUTE TO AZOMETHINE YLIDES - BACKGROUND AND REACTION OF AMINES WITH BIFUNCTIONAL KETONES [J].

ARDILL, H ;

DORRITY, MJR ;

GRIGG, R ;

LEONLING, MS ;

MALONE, JF ;

SRIDHARAN, V ;

THIANPATANAGUL, S .

TETRAHEDRON, 1990, 46 (18) :6433-6448

[3] Synthesis of pyrrolizidine derivatives by 1,3-dipolar cycloaddition reactions of chiral five-membered cyclic azomethine ylides [J].

Argyropoulos, Nikolaos G. ;

Sarli, Vasiliki C. ;

Gdaniec, Maria .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (16) :3738-3745

[4] Radical reactions with 3H-quinazolin-4-ones:: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin [J].

Bowman, W. Russell ;

Elsegood, Mark R. J. ;

Stein, Tobias ;

Weaver, George W. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (01) :103-113

[5]

BRAEKMAN JC, 1987, Z NATURFORSCH C, V42, P627

[6] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles [J].

Campos, Kevin R. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1069-1084

[7] A facile total synthesis of rutaecarpine [J].

Chavan, SP ;

Sivappa, R .

TETRAHEDRON LETTERS, 2004, 45 (05) :997-999

[8] Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].

Coldham, I ;

Hufton, R .

CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809

[9] Chemistry of the hexahydropyrrolo[2,3-b]indoles:: Configuration, conformation, reactivity, and applications in synthesis [J].

Crich, David ;

Banerjee, Abhisek .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (02) :151-161

[10]

Friedla''nder P., 1883, Ber. Dtsch. Chem. Ges, V16, P1833, DOI DOI 10.1002/CBER.18830160265

← 1 2 3 4 →