Synthesis of pyrazine alealoids from Botryllus leachi.: Diazines 43

被引:50
作者
Buron, F [1 ]
Plé, N [1 ]
Turck, A [1 ]
Queguiner, G [1 ]
机构
[1] INSA, UMR 6014, Lab Chim Organ Fine & Heterocycl, F-76131 Mont St Aignan, France
关键词
D O I
10.1021/jo0478196
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regioselective metalation of pyrazines and cross-coupling reactions provides an easy access to botryllazines A and B and to an isomer of botryllazine A with good yields from chloropyrazine.
引用
收藏
页码:2616 / 2621
页数:6
相关论文
共 18 条
[1]   OPTIMIZATION AND APPLICATION OF LITHIUM PARAMETERS FOR PM3 [J].
ANDERS, E ;
KOCH, R ;
FREUNSCHT, P .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1993, 14 (11) :1301-1312
[2]   CARBANIONS OF 1,3-DITHIANES . REAGENTS FOR C-C BOND FORMATION BY NUCLEOPHILIC DISPLACEMENT AND CARBONYL ADDITION [J].
COREY, EJ ;
SEEBACH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1965, 4 (12) :1075-&
[3]   Novel alkaloids from the red ascidian Botryllus leachi [J].
Durán, R ;
Zubía, E ;
Ortega, MJ ;
Naranjo, S ;
Salvá, J .
TETRAHEDRON, 1999, 55 (46) :13225-13232
[4]   Lithiation of 2-chloro- and 2-methoxypyridine with lithium dialkylamides: Initial ortho-direction or subsequent lithium ortho-stabilization? [J].
Gros, P ;
Choppin, S ;
Fort, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2243-2247
[5]   Lithiation of 2-(chloroaryl)-2-methyl-1,3-dioxolanes and application in synthesis of new ortho-functionalized acetophenone derivatives [J].
Lukacs, G ;
Porcs-Makkay, M ;
Simig, G .
TETRAHEDRON LETTERS, 2003, 44 (15) :3211-3214
[6]  
Mahboobi S, 2004, MONATSH CHEM, V135, P333, DOI 10.1007/s00706-003-0085-2
[7]   Several approaches to cyanide ion-catalyzed synthesis of 4-aroyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidines [J].
Miyashita, A ;
Suzuki, Y ;
Ohta, K ;
Iwamoto, K ;
Higashino, T .
HETEROCYCLES, 1998, 47 (01) :407-414
[8]   Aroylation of fused pyrimidines; Synthesis of 4-aroylfuro[2,3-d]-, 4-aroylthieno[2,3-d]-, and 4-aroylisoxazolo[5,4-d]pyrimidines [J].
Miyashita, A ;
Obae, K ;
Suzuki, Y ;
Oishi, E ;
Iwamoto, K ;
Higashino, T .
HETEROCYCLES, 1997, 45 (11) :2159-2173
[9]  
MIYASHITA A, 1994, CHEM PHARM BULL, V42, P2107