TANDEM INTERMOLECULAR-INTRAMOLECULAR MICHAEL ADDITION OF BIFUNCTIONAL HETERO NUCLEOPHILES TO POLYFLUORO-2-ALKYNOIC ACIDS - FACILE SYNTHESIS OF POLYFLUOROALKYLATED AZAHETEROCYCLES

被引：21

作者：

FUNABIKI, K ^{[1
]}

TAMURA, K ^{[1
]}

ISHIHARA, T ^{[1
]}

YAMANAKA, H ^{[1
]}

机构：

[1] KYOTO INST TECHNOL, DEPT CHEM & MAT TECHNOL, SAKYO KU, KYOTO 606, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1994年 / 67卷 / 11期

关键词：

D O I：

10.1246/bcsj.67.3021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Polyfluoro-2-alkynoic acids, R(f)-C drop C-COOH (1a-c: a, R(f)=CHF2; b, R(f)=CF3; c, R(f)=CHF2CF2CF2), readily underwent an intermolecular-intramolecular Michael addition reaction with a variety of bifunctional azanucleophiles, such as RNHCH(2)CH(2)XH (R=H, Me; X=NH, S, O, NMe) and o-phenylenediamine, to give the corresponding carboxylated and/or decarboxylated 2-(polyfluoroalkyl)imidazolidine, thiazolidine, and oxazolidine derivatives in moderate to good yields.

引用

收藏

页码：3021 / 3029

页数：9

相关论文

共 34 条

[11] SYNTHESIS OF 2F-ALKYL-4-HYDROXYQUINOLINES [J].

FROISSARD, J ;

GREINER, J ;

PASTOR, R ;

CAMBON, A .

JOURNAL OF FLUORINE CHEMISTRY, 1981, 17 (03) :249-263

[12] RING-CHAIN TAUTOMERISM IN 1,3-THIAZOLIDINES [J].

FULOP, F ;

MATTINEN, J ;

PIHLAJA, K .

TETRAHEDRON, 1990, 46 (18) :6545-6552

[13] SYNTHESIS AND REACTIVITY OF NEW PERFLUOROALKYL SYNTHONS - ATYPICAL BEHAVIOR OF F-ALKYLATED AZIRINES AND AZIRIDINES [J].

HADDACH, M ;

PASTOR, R ;

RIESS, JG .

TETRAHEDRON, 1993, 49 (21) :4627-4638

[14] SYNTHESIS OF NEW F-ALKYLATED AMINO-ACIDS DERIVED FROM LYSINE, ARGININE AND CYSTEINE [J].

HADDACH, M ;

PASTOR, R ;

RIESS, JG .

JOURNAL OF FLUORINE CHEMISTRY, 1991, 51 (02) :197-205

[15] CYCLOCONDENSATION OF ALKYLHYDRAZINES AND BETA-SUBSTITUTED ACETYLENIC ESTERS - SYNTHESIS OF 3-HYDROXYPYRAZOLES [J].

HAMPER, BC ;

KURTZWEIL, ML ;

BECK, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5680-5686

[16] REGIOSELECTIVE SYNTHESIS OF 1-METHYL-3-HYDROXY-5-PERFLUOROALKYLPYRAZOLES BY THE ADDITION OF METHYLHYDRAZINE TO PERFLUOROALKYLACETYLENIC ESTERS [J].

HAMPER, BC .

JOURNAL OF FLUORINE CHEMISTRY, 1990, 48 (01) :123-131

[17]

HUANG YZ, 1982, SCI SIN B-CHEM B A M, V25, P587

[18]

HUANG YZ, 1982, SCI SIN B-CHEM B A M, V25, P21

[19] STEREOELECTRONIC EFFECTS IN THE FORMATION OF 5-MEMBERED AND 6-MEMBERED RINGS - THE ROLE OF BALDWIN RULES [J].

JOHNSON, CD .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (09) :476-482

[20] 4-FLUORO-2-BUTYNAL - PREPARATION AND SOME EXAMPLES OF DIENOPHILIC PROPERTIES [J].

KHANOUS, A ;

GORGUES, A ;

COUSSEAU, J .

JOURNAL OF FLUORINE CHEMISTRY, 1990, 49 (03) :401-408

← 1 2 3 4 →