LITHIUM MIGRATION IN THE PYRIDINE SERIES - DOUBLE CATALYSIS AND REFORMING - SYNTHESIS OF DERIVATIVES OF 2-BROMO-3-LITHIO-PYRIDINE AND 4-BROMO-2-HALOGENO-3-LITHIO-PYRIDINES

被引:66
作者
MALLET, M
BRANGER, G
MARSAIS, F
QUEGUINER, G
机构
[1] Laboratoire de Chimie Organique Fine et Hétérocyclique de l'IRCOF, INSA de Rouen, 76130 Mont Saint Aignan
关键词
D O I
10.1016/0022-328X(90)80210-Q
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The lithium of an organolithio-pyridinic derivative can be moved from one position to an other by an intermolecular reaction. Two new reactions are possible for pyridinic organic synthesis: the isomerisation of any lithio derivative to a more stable one, and a reaction that transforms a mixture of various bromo-lithio derivatives into a single one. The processes involved and the experimental tools used are described in terms of the 2-bromo-3-lithio- and 4-bromo-2-halogeno-3-lithio-pyridines derivatives synthesis. © 1990.
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页码:319 / 332
页数:14
相关论文
共 28 条
[1]  
BOLD P, 1966, TETRAHEDRON LETT, V30, P3599
[2]   SYNTHESIS OF 3-HYDROXYPYRIDINE AND 2H-PYRANO[2,3-B]PYRIDIN-2-ONES [J].
BONNETAUD, D ;
PASTOUR, P ;
QUEGUINER, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1972, 9 (01) :165-+
[3]   ISOMERIZATION AND DISPROPORTIONATION OF TRIHALOBENZENES CATALYZED BY POTASSIUM ANILIDE IN LIQUID AMMONIA [J].
BUNNETT, JF ;
MOYER, CE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (05) :1183-&
[4]   BASE-CATALYZED HALOGEN DANCE, AND OTHER REACTIONS OF ARYL HALIDES [J].
BUNNETT, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 1972, 5 (04) :139-&
[5]   REMARKABLE REACTIVITY OF ARYL HALIDES WITH NUCLEOPHILES [J].
BUNNETT, JF .
JOURNAL OF CHEMICAL EDUCATION, 1974, 51 (05) :312-315
[6]   1-LITHIOISOBENZOFURAN AND 1,3-DILITHIOISOBENZOFURAN - FORMATION AND REACTIONS WITH ELECTROPHILES [J].
CRUMP, SL ;
RICKBORN, B .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) :304-310
[7]   PREPARATION OF ISOBENZOFURAN ARYNE CYCLOADDUCTS [J].
CRUMP, SL ;
NETKA, J ;
RICKBORN, B .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15) :2746-2750
[8]  
DAVIES GM, 1972, TETRAHEDRON LETT, V33, P3507
[9]  
DESILVA SO, 1978, TETRAHEDRON LETT, V51, P5107
[10]   EFFECTS OF ALKYL-GROUPS ON RATES OF SN2 REACTIONS [J].
DETAR, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (25) :5174-5176