Cycloaddition reactions of phosphorylated 1,2-diaza-1,3-butadienes with olefins:: Regioselective synthesis of pyridazine derivatives

被引：38

作者：

Palacios, F ^{[1
]}

Aparicio, D ^{[1
]}

López, Y ^{[1
]}

Santos, JMD ^{[1
]}

Alonso, C ^{[1
]}

机构：

[1] Univ Basque Country, Fac Farm, Dept Quim Organ 1, Vitoria 01080, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 06期

关键词：

cycloadditions; diazabutadienes; hydrazones; fused-ring systems; nitrogen heterocycles;

D O I：

10.1002/ejoc.200400675

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aza-Diels-Alder reaction of 4-phosphinyl- and 4-phosphonyl-1,2-diaza-1,3-butadienes with styrene, cyclopentadiene, dihydrofuran and norbornadiene is reported. Monocyclic, bicyclic and polycyclic tetrahydropyridazines containing a phosphane oxide or a phosphonate substituent are obtained. The formation of cycloadducts can be explained by an endo transition state in the cycloaddition process of these heterodienes with styrene, cyclopentadiene, dihydrofuran, and by means of an exo transition state in the case of norbornadiene. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheirn, Germany, 2005).

引用

页码：1142 / 1147

页数：6

共 67 条

[11] The first density functional study on the [4+2]-cycloaddition reactions of 1,2-diaza-1,3-butadiene with alkenes [J].

Avalos, M ;

Babiano, R ;

Clemente, FR ;

Cintas, P ;

Gordillo, R ;

Jiménez, JL ;

Palacios, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8251-8259

[12] Experimental and theoretical insights regarding the cycloaddition reaction of carbohydrate-based 1,2-diaza-1,3-butadienes and acrylonitrile.: A model case for the behavior of chiral azoalkenes and unsymmetric olefinst [J].

Avalos, M ;

Babiano, R ;

Cintas, P ;

Clemente, FR ;

Gordillo, R ;

Jiménez, JL ;

Palacios, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2241-2251

[13] Synergic effect of vicinal stereocenters in [3+2] cycloadditions of carbohydrate azadipolarophiles and mesoionic dipoles:: Origin of diastereofacial selectivity [J].

Avalos, M ;

Babiano, R ;

Cintas, P ;

Clemente, FR ;

Gordillo, R ;

Jiménez, JL ;

Palacios, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (15) :5139-5145

[14] 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

[15] REARRANGEMENT REACTIONS .3. SYNTHESES AND DIELS-ALDER REACTIONS OF 2-ALKYLAZO-SUBSTITUTED 1,3-BUTADIENES [J].

BANERT, K ;

HAGEDORN, M .

TETRAHEDRON LETTERS, 1992, 33 (48) :7331-7334

[16] New heterocyclic precursors for thermal generation of reactive, electron-rich 1,2-diaza-1 3-butadienes [J].

Boeckman, RK ;

Ge, P ;

Reed, JE .

ORGANIC LETTERS, 2001, 3 (23) :3647-3650

[17] Recent developments in imino Diels-Alder reactions [J].

Buonora, P ;

Olsen, JC ;

Oh, T .

TETRAHEDRON, 2001, 57 (29) :6099-6138

[18] DIASTEREOFACIAL SELECTIVITY IN UNCATALYZED DIELS-ALDER CYCLOADDITIONS INVOLVING ALPHA, BETA-UNSATURATED ESTERS AND LACTONES WITH STEREOGENIC CENTERS CONTAINING OXYGEN FUNCTIONALITIES [J].

CASAS, R ;

PARELLA, T ;

BRANCHADELL, V ;

OLIVA, A ;

ORTUNO, RM ;

GUINGANT, A .

TETRAHEDRON, 1992, 48 (13) :2659-2680

[19] COMPETING [4 + 2] AND [3 + 2] CYCLOADDITION IN THE REACTIONS OF NUCLEOPHILIC OLEFINS WITH ETHYL 3-(TOLUENE-PARA-SULPHONYLAZO)BUT-2-ENOATE [J].

CLARKE, SJ ;

DAVIES, DE ;

GILCHRIST, TL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1803-1807

[20] REACTIONS OF AZOALKENES DERIVED FROM HYDRAZONES OF ETHYL BROMOPYRUVATE WITH ELECTRON RICH ALKENES AND HETEROCYCLES [J].

CLARKE, SJ ;

GILCHRIST, TL ;

LEMOS, A ;

ROBERTS, TG .

TETRAHEDRON, 1991, 47 (29) :5615-5624

← 1 2 3 4 5 6 7 →