Novel synthesis of the ocular age pigment A2-E: New method for substituted pyridine synthesis via azaelectrocyclization

被引：67

作者：

Tanaka, K ^{[1
]}

Katsumura, S ^{[1
]}

机构：

[1] Kwansei Gakuin Univ, Sch Sci, Nishinomiya, Hyogo 6628501, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 03期

关键词：

D O I：

10.1021/ol991320u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The formal synthesis of the ocular age pigment A2-E was achieved by the efficient one-pot preparation of the substituted pyridine, which involves the aza-6 pi-electrocyclization of the Schiff base derived from (E)-3-carbonyl-2,4,6-trienal followed by oxidation.

引用

收藏

页码：373 / 375

页数：3

相关论文

共 26 条

[1] BETA-LACTAMS FROM ESTERS AND SILYLIMINES - A REVALUATION - SYNTHESIS OF N-UNSUBSTITUTED 4-ALKYL-BETA-LACTAMS [J].

CAINELLI, G ;

GIACOMINI, D ;

PANUNZIO, M ;

MARTELLI, G ;

SPUNTA, G .

TETRAHEDRON LETTERS, 1987, 28 (44) :5369-5372

[2] ON THE THERMAL-BEHAVIOR OF SCHIFF-BASES OF RETINAL AND ITS ANALOGS - 1,2-DIHYDROPYRIDINE FORMATION VIA 6-PI-ELECTRON ELECTROCYCLIZATION OF 13-CIS ISOMERS [J].

DELERA, AR ;

REISCHL, W ;

OKAMURA, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4051-4063

[3] PREPARATION AND REACTIONS OF SOME HALOPHOSPHORANES [J].

DENNEY, DB ;

ROSS, ST .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (03) :998-&

[4] REDUCTION OF CHLORANIL BY DIHYDROPYRIDINES IN SOLID-SOLUTIONS - INFRARED STUDY OF REACTION-RATE [J].

DOMMISSE, R ;

DESSEYN, HO ;

ALDERWEI.FC .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1973, A 29 (01) :107-113

[5]

Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01

[6]

FEENEYBURNS L, 1984, INVEST OPHTH VIS SCI, V25, P195

[7] PREPARATION OF PRIMARY AMINES AND 2-AZETIDINONES VIA N-TRIMETHYLSILYL IMINES [J].

HART, DJ ;

KANAI, K ;

THOMAS, DG ;

YANG, TK .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) :289-294

[8] Enantioselective total syntheses of ircinal A and related manzamine alkaloids [J].

Martin, SF ;

Humphrey, JM ;

Ali, A ;

Hillier, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :866-867

[9]

Marvell E.N., 1980, Thermal Electrocyclic Reactions

[10] 6-PI-ELECTROCYCLIZATION OF 1-AZATRIENES TO 1,2-DIHYDROPYRIDINES [J].

MAYNARD, DF ;

OKAMURA, WH .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1763-1771