A novel and practical method for hydrocyanation of chalcones

被引：12

作者：

Ellis, JE ^{[1
]}

Davis, EM ^{[1
]}

Brower, PL ^{[1
]}

机构：

[1] Warner Lambert Co, Parke Davis Pharmaceut Res Div, Chem Dev Dept, Holland, MI 49424 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 1997年 / 1卷 / 03期

关键词：

D O I：

10.1021/op960048q

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel and practical method for the hydrocyanation of chalcones is described, The chalcone hydrocyanation reaction proceeds very efficiently using only 125 mol % of acetone cyanohydrin and 5 mol % of tetramethylammonium hydroxide. This reaction stoichiometry provides high-quality product in good yield on pilot scale, In addition, the reduced amounts of acetone cyanohydrin improve the workup, in which the excess cyanide is destroyed with sodium hypochlorite.

引用

页码：250 / 252

页数：3

共 12 条

[1]

BETTS BE, 1958, J CHEM SOC, P4193

[2]

BRETHERECK L, 1979, HDB REACTIVE CHEM HA, P805

[3] CHALCONES AND RELATED COMPOUNDS .4. ADDITION OF HYDROGEN CYANIDE TO CHALCONES [J].

DAVEY, W ;

TIVEY, DJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (MAR) :1230-1236

[4] DISCOVERY OF A NOVEL SERIES OF ORALLY-ACTIVE NONPEPTIDE ENDOTHELIN-A (ET(A)) RECEPTOR-SELECTIVE ANTAGONISTS [J].

DOHERTY, AM ;

PATT, WC ;

EDMUNDS, JJ ;

BERRYMAN, KA ;

REISDORPH, BR ;

PLUMMER, MS ;

SHAHRIPOUR, A ;

LEE, C ;

CHENG, XM ;

WALKER, DM ;

HALEEN, SJ ;

KEISER, JA ;

FLYNN, MA ;

WELCH, KM ;

HALLAK, H ;

TAYLOR, DG ;

REYNOLDS, EE .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (08) :1259-1263

[5] STUDIES ON THE CHEMICAL-CONSTITUENTS OF RUTACEOUS PLANTS .62. EFFICIENT SYNTHESIS OF FAGARONINE, A PHENOLIC BENZO[C]PHENANTHRIDINE ALKALOID WITH ANTILEUKEMIC ACTIVITY [J].

ISHII, H ;

CHEN, IS ;

ISHIKAWA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03) :671-676

[6]

JENKS WR, 1979, ENCY CHEM TECHNOLOGY, V7, P320

[7]

Kohler E. P., 1941, ORG SYNTH, V1, P78

[8] Experiments on substituted allenecarboxylic acids Part I [J].

Lapworth, A ;

Wechsler, E .

JOURNAL OF THE CHEMICAL SOCIETY, 1910, 97 :38-48

[9]

LIOTTA CL, 1977, TETRAHEDRON LETT, P1117

[10] ACID-CATALYZED CONDENSATIONS .2. THE CONDENSATION OF BENZALDEHYDE WITH SUBSTITUTED ACETOPHENONES [J].

LYLE, RE ;

PARADIS, LP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (24) :6667-6668

← 1 2 →