Regio- and stereoselective one-pot synthesis of unknown oxazoline-fused pyridazines by 'Michael addition-pyridazine cyclization-oxazoline cyclization' cascade reactions of 4-chloro-1,2-diaza-1,3-butadienes with 3-dimethylaminopropenoates

被引：25

作者：

Attanasi, Orazio A. ^{[1
]}

Favi, Gianfranco ^{[1
]}

Filippone, Paolino ^{[1
]}

Golobic, Amalija ^{[2
]}

Perrulli, Francesca R. ^{[1
]}

Stanovnik, Branko ^{[2
]}

Svete, Jurij ^{[2
]}

机构：

[1] Univ Urbino, Inst Chim Organ, I-61029 Urbino, Italy

[2] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia

来源：

SYNLETT | 2007年 / 19期

关键词：

1,2-diaza-1,3-butadienes; 3-dimethylaminopropenoates; Michael additions; cyclizations; oxazoline-fused pyridazines;

D O I：

10.1055/s-2007-990962

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot, three-step regio- and stereoselective synthesis of unknown functionalized oxazoline-fused pyridazines is reported. The approach involves base-assisted `Michael addition-pyridazine cyclization-oxazoline cyclization' cascade reactions of 4-chloro1,2-diaza-1,3-butadienes with 3-dimethylaminopropenoates.

引用

页码：2971 / 2974

页数：4

共 59 条

[21] DIELS-ALDER REACTIONS OF AZADIENES [J].

BOGER, DL .

TETRAHEDRON, 1983, 39 (18) :2869-2939

[22]

CADEZ Z, 1990, SYNTHESIS-STUTTGART, P70

[23] ENZYMATIC FORMATION OF SESQUITERPENES [J].

CANE, DE .

CHEMICAL REVIEWS, 1990, 90 (07) :1089-1103

[24] Tandem and domino catalytic strategies for enantioselective synthesis [J].

Chapman, Christopher J. ;

Frost, Christopher G. .

SYNTHESIS-STUTTGART, 2007, (01) :1-21

[25] A highly diastereoselective approach to conformationally constrained serine analogues:: Synthesis of an α-amino-β-hydroxycyclohexenecarboxylic acid and derivatives [J].

Clerici, F ;

Gelmi, ML ;

Gambini, A .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :5764-5767

[26] Asymmetric organocatalytic domino reactions [J].

Enders, Dieter ;

Grondal, Christoph ;

Huettl, Matthias R. M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581

[27]

Fringuelli F., 2002, The Diels-Alder Reaction: Selected Practical Methods

[28]

Fringuelli F., 1990, Dienes in the Diels-Alder Reaction

[29] ADDITION AND CYCLO-ADDITION REACTIONS OF BETA-CHLOROAZO-OLEFINS [J].

GILCHRIST, TL ;

STEVENS, JA ;

PARTON, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08) :1741-1745

[30]

Loughlin WA, 2004, CHEM REV, V104, P6085, DOI 10.1021/cr040648k

← 1 2 3 4 5 6 →