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

[1]

Albert M., 2006, TOP CURR CHEM, V264, P1, DOI DOI 10.1007/128_026

[2]

[Anonymous], 1979, ANGEW CHEM, V91, P756

[3] Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions [J].

Aparicio, Domitila ;

Attanasi, Orazio A. ;

Filippone, Paolino ;

Ignacio, Roberto ;

Lillini, Samuele ;

Mantellini, Fabio ;

Palacios, Francisco ;

Santos, Jesus M. de los .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :5897-5905

[4] EFFECT OF METAL-IONS IN ORGANIC-SYNTHESIS .28. SYNTHESIS OF NEW 1-AROYLAMINO-3-AMINOCARBONYLPYRROLES [J].

ATTANASI, O ;

GROSSI, M ;

SERRAZANETTI, F .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1986, 18 (1-2) :1-5

[5]

ATTANASI O, 1984, SYNTHESIS-STUTTGART, P671

[6]

ATTANASI O, 1984, SYNTHESIS-STUTTGART, P873

[7] Efficient synthesis and environmentally friendly reactions of PEG-supported 1,2-diaza-1,3-butadiene [J].

Attanasi, OA ;

De Crescentini, L ;

Favi, G ;

Filippone, P ;

Lillini, S ;

Mantellini, F ;

Santeusanio, S .

ORGANIC LETTERS, 2005, 7 (12) :2469-2471

[8] Unexpected behavior of the reaction between 1,2-diaza-1,3-butadienes and 3-dimethylaminopropenoates: A useful entry to new pyrrolines, pyrroles, and oxazolines [J].

Attanasi, OA ;

Favi, G ;

Filippone, P ;

Golobic, A ;

Stanovnik, B ;

Svete, J .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4307-4313

[9] Solvent-free reaction of some 1,2-diaza-1,3-butadienes with phosphites:: Environmentally friendly access to new diazaphospholes and E-hydrazonophosphonates [J].

Attanasi, OA ;

Baccolini, G ;

Boga, C ;

De Crescentini, L ;

Filippone, P ;

Mantellini, F .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4033-4037

[10] Access to new 2-oxofuro[2,3-b]pyrroles and 2-methylenepyrroles through the reaction of 1,2-diaza-1,3-butadienes and γ-ketoesters [J].

Attanasi, OA ;

De Crescentini, L ;

Favi, G ;

Filippone, P ;

Mantellini, F ;

Santeusanio, S .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) :2686-2692

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