3-BROMO-2-PYRONE - AN EASILY PREPARED CHAMELEON DIENE AND A SYNTHETIC EQUIVALENT OF 2-PYRONE IN THERMAL DIELS-ALDER CYCLOADDITIONS

被引：52

作者：

POSNER, GH

NELSON, TD

KINTER, CM

AFARINKIA, K

机构：

[1] Department of Chemistry, The Johns Hopkins University, Baltimore

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 39期

关键词：

D O I：

10.1016/S0040-4039(00)92368-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Bromo-2-pyrone, a stable solid prepared by a new route (eq. 1), has been found to undergo smooth and regiospecific 2+4-cycloadditions between 78-90-degrees-C with both electron-rich and electron-deficient dienophiles; subsequent high-yield reductive debrominations produced halogen-free cycloadducts thus showing 3-bromo-2-pyrone to be a practical and effective synthetic equivalent of 2-pyrone in thermal Diels-Alder cycloadditions.

引用

收藏

页码：5295 / 5298

页数：4

相关论文

共 32 条

[1] DIELS-ALDER REACTION OF ALPHA-PYRONES WITH ELECTRON-RICH OLEFINS [J].

BEHRINGER, H ;

HECKMAIER, P .

CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (08) :2835-+

[2] TOTAL SYNTHESES OF AZAFLUORANTHENE ALKALOIDS - RUFESCINE AND IMELUTEINE [J].

BOGER, DL ;

BROTHERTON, CE .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :4050-4055

[3] INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 3-CARBOMETHOXY-2-PYRONES - CONTROLLED INTRODUCTION OF OXYGENATED AROMATICS - BENZENE, PHENOL, CATECHOL, RESORCINOL, AND PYROGALLOL ANNULATION - REGIOSPECIFIC TOTAL SYNTHESIS OF SENDAVERINE AND A PREPARATION OF 6,7-BENZOMORPHANS [J].

BOGER, DL ;

MULLICAN, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :4033-4044

[4] TOTAL SYNTHESIS OF (+/-)-ALPHA- AND (+/-)-BETA-COPAENES AND YLANGENES [J].

COREY, EJ ;

WATT, DS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (07) :2303-2311

[5] INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 4,6-DIMETHYL-2-OXO-2H-PYRAN-5-CARBOXYLIC ACID-ESTERS AND MORPHOLINO ENAMINES - REGIOSPECIFIC PREPARATION OF "3-SUBSTITUTED-2,6-DIMETHYLBENZOATES OR "4-SUBSTITUTED-2,6-DIMETHYLBENZOATES [J].

GINGRICH, HL ;

ROUSH, DM ;

VANSAUN, WA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :4869-4873

[6] HIGH-PRESSURE CYCLOADDITIONS OF PYRONES - SYNTHESIS OF HIGHLY FUNCTIONALIZED 6-MEMBERED RINGS BY INHIBITION OF CARBON-DIOXIDE LOSS [J].

GLADYSZ, JA ;

LEE, SJ ;

TOMASELLO, JAV ;

YU, YS .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (25) :4170-4172

[7] CYCLOADDITIONS OF ISOQUINOLINIUM SALTS - EVIDENCE FOR A 2-STEP MECHANISM IN A STEREOCONTROLLED SYNTHESIS OF SUBSTITUTED TETRALINS [J].

GUPTA, RB ;

FRANCK, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5393-5403

[8]

HARANO K, 1990, CHEM PHARM BULL, V38, P1182

[9]

HERDEIS C, 1991, LIEBIGS ANN CHEM, P99

[10] A CHIRAL SYNTHESIS OF THE LEFT-SIDE ALDEHYDE FOR LASALOCID A SYNTHESIS [J].

IRELAND, RE ;

MCGARVEY, GJ ;

ANDERSON, RC ;

BADOUD, R ;

FITZSIMMONS, B ;

THAISRIVONGS, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (19) :6178-6180

← 1 2 3 4 →