3,4,6-trisubstituted-2-pyrone synthesis via the nucleophilic addition of 2-alkyl Meldrum's acid to alkynyl ketone

被引:4
作者
Hachiya, I [1 ]
Shibuya, H [1 ]
Hanai, K [1 ]
Shimizu, M [1 ]
机构
[1] Mie Univ, Dept Chem Mat, Tsu, Mie 5148507, Japan
关键词
2-pyrone; Meldrum's acid; alkynyl ketone; dialkynyl ketone;
D O I
10.2174/1570178043400505
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3,4,6-Trisubstituted-2-pyrone synthesis via the nucleophilic addition of 2-alkyl Meldrum's acid to alkynyl ketone has been developed. The reaction of 2-alkyl Meldrum's acid with alkynyl ketones provided 3,4,6-trisubstituted-2-pyrones in good yields. The reaction of dialkynyl ketones gave 6-alkynyl-2-pyrones.
引用
收藏
页码:349 / 352
页数:4
相关论文
共 13 条
[1]   DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].
AFARINKIA, K ;
VINADER, V ;
NELSON, TD ;
POSNER, GH .
TETRAHEDRON, 1992, 48 (42) :9111-9171
[2]   PHARMACOLOGY AND TOXICOLOGY OF TOAD VENOM [J].
CHEN, KK ;
KOVARIKOVA, A .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1967, 56 (12) :1535-+
[3]   Novel 2-pyrone synthesis via the nucleophilic addition. of active methine compounds to 2-alkynone [J].
Hachiya, I ;
Shibuya, H ;
Shimizu, M .
TETRAHEDRON LETTERS, 2003, 44 (10) :2061-2063
[4]  
HAYASHI Y, 1977, TETRAHEDRON LETT, P3637
[5]   SYNTHETIC APPLICATIONS OF DEALKOXYCARBONYLATIONS OF MALONATE ESTERS, BETA-KETO-ESTERS, ALPHA-CYANO ESTERS AND RELATED-COMPOUNDS IN DIPOLAR APROTIC MEDIA .2. [J].
KRAPCHO, AP .
SYNTHESIS-STUTTGART, 1982, (11) :893-914
[6]   TUMOR INHIBITORS .65. BERSENOGENIN, BERSCILLOGENIN, AND 3-EPIBERSCILLOGENIN, 3 NEW CYTOTOXIC BUFADIENOLIDES FROM BERSAMA-ABYSSINICA [J].
KUPCHAN, SM ;
MONIOT, JL ;
SIGEL, CW ;
HEMINGWAY, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (18) :2611-+
[7]   K2CO3-catalyzed Michael addition -: Lactonization reaction of 1,2-allenyl ketones with electron-withdrawing group substituted acetates.: An efficient synthesis of α-pyrone derivatives [J].
Ma, SM ;
Yin, SH ;
Li, LT ;
Tao, FG .
ORGANIC LETTERS, 2002, 4 (04) :505-507
[8]   An efficient synthesis of 4-alkenyl/alkynyl-6-methyl-2-pyrones via Pd-catalysed coupling on 4-bromo-6-methyl-2-pyrone [J].
Marrison, LR ;
Dickinson, JM ;
Ahmed, R ;
Fairlamb, IJS .
TETRAHEDRON LETTERS, 2002, 43 (49) :8853-8857
[9]  
PRASAD JVNV, 1994, J AM CHEM SOC, V116, P6989
[10]   TOTAL SYNTHESIS OF (+/-)-ASTELTOXIN [J].
SCHREIBER, SL ;
SATAKE, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (15) :4186-4188