A facile and convenient synthesis of 1,2,3,6-tetrahydropyridazines using azodicarboxylates under lanthanum triflate catalysis

被引：16

作者：

Curini, M ^{[1
]}

Epifano, F ^{[1
]}

Marcotullio, MC ^{[1
]}

Rosati, O ^{[1
]}

机构：

[1] Univ Perugia, Fac Farm, Sezione Chim Organ, Dipartimento Chim & Tecnol Farm, I-06123 Perugia, Italy

来源：

HETEROCYCLES | 2001年 / 55卷 / 08期

关键词：

D O I：

10.3987/COM-01-9272

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hetero-Diels-Alder reaction catalyzed by lanthanum triflate hydrate using diethyl azodicarboxylate as dienophile, yielding differently substituted 1,2,3,6-tetrahydropyridazines, is described.

引用

页码：1599 / 1604

页数：6

共 21 条

[1] Asymmetric synthesis of (3S)-2,3,4,5-tetrahydropyridazine-3-carboxylic acid and its methyl ester [J].

Aspinall, IH ;

Cowley, PM ;

Mitchell, G ;

Raynor, CM ;

Stoodley, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (18) :2591-2599

[2] Hetero-Diels-Alder reactions of homochiral 1,2-diaza-1,3-butadienes with diethyl azodicarboxylate under microwave irradiation.: Theoretical rationale of the stereochemical outcome [J].

Avalos, M ;

Babiano, R ;

Cintas, P ;

Clemente, FR ;

Jiménez, JL ;

Palacios, JC ;

Sánchez, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17) :6297-6305

[3]

CURINI M, 2001, TETRAHEDRON LETT, V42, P3159

[4] SOLVENT EFFECT AS THE RESULT OF FRONTIER MOLECULAR-ORBITAL INTERACTION .5. DIELS-ALDER WITH HETERODIENOPHILES - A UNIFIED APPROACH TO THE SOLVENT EFFECT OF THE DIELS-ALDER REACTIONS [J].

DESIMONI, G ;

FAITA, G ;

RIGHETTI, PP ;

TOMA, L .

TETRAHEDRON, 1990, 46 (23) :7951-7970

[5]

Diels O, 1925, LIEBIGS ANN CHEM, V443, P242

[6] A C-13 NMR-STUDY OF SOME DI-HYDROPYRIDAZINES, TETRA-HYDROPYRIDAZINES, AND HEXA-HYDROPYRIDAZINES [J].

FISHER, TH ;

CROOK, JC ;

CHANG, S .

TETRAHEDRON, 1987, 43 (11) :2443-2450

[7] DENOVO-SYNTHESIS OF CARBOHYDRATES - PREPARATION OF 4-AMINO-4-DEOXY-D,L-RIBOSE DERIVATIVES [J].

FORREST, AK ;

SCHMIDT, RR .

TETRAHEDRON LETTERS, 1984, 25 (17) :1769-1772

[8] DIELS-ALDER SYNTHESES WITH 1,4-DI-TERT-BUTOXY-1,3-BUTADIENE [J].

HIRANUMA, H ;

MILLER, SI .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (18) :3096-3102

[9] ANATOMY OF ENE AND DIELS-ALDER REACTIONS BETWEEN CYCLOHEXADIENES AND AZODICARBOXYLATES [J].

JENNER, G ;

SALEM, RB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (11) :1961-1964

[10] THE SYNTHESIS OF NATURAL HETEROCYCLIC PRODUCTS BY HETERO DIELS-ALDER CYCLO-ADDITION REACTIONS [J].

KAMETANI, T ;

HIBINO, S .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1987, 42 :245-333

← 1 2 3 →