The synthesis of three new heterocycles:: the pyrido[4,3 or 3,4 or 2,3-c]-1,5-naphthyridines

被引:20
作者
Cailly, Thomas
Fabis, Frederic
Legay, Remi
Oulyadi, Hassan
Rault, Sylvain [1 ]
机构
[1] Univ Caen, Ctr Etud & Rech Medicament Normandie, UFR Sci Pharmaceut, F-14032 Caen, France
[2] Univ Rouen, Lab RMN, IRCOF, UMR 6014,CNRS, F-76821 Mont St Aignan, France
关键词
D O I
10.1016/j.tet.2006.10.046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrido[4,3 or 3,4 or 2,3-c]-1,5-naphthyridines were obtained with good yields after chlorodehydroxylation and dehalogenation reactions starting from the parent pyridonaphthyridinones. These pyridonaphthyridinones were synthesized in a two-step procedure using a Suzuki cross-coupling reaction between 2-chloro-3-fluoropyridine and orthocyanopyridylboronic esters followed by a KOH-mediated anionic ring closure. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:71 / 76
页数:6
相关论文
共 19 条
[1]   Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling [J].
Arvela, RK ;
Leadbeater, NE .
ORGANIC LETTERS, 2005, 7 (11) :2101-2104
[2]   Selective functionalization of 2-fluoropyridine, 2,3-difluoropyridine, and 2,5-difluoropyridine at each vacant position [J].
Bobbio, C ;
Schlosser, M .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3039-3045
[3]   An efficient two-step total synthesis of the quaterpyridine nemertelline [J].
Bouillon, A ;
Voisin, AS ;
Robic, A ;
Lancelot, JC ;
Collot, V ;
Rault, S .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10178-10180
[4]   Synthesis of novel halopyridinylboronic acids and esters. Part 3: 2, or 3-halopyridin-4-yl-boronic acids and esters [J].
Bouillon, A ;
Lancelot, JC ;
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 2002, 58 (22) :4369-4373
[5]   Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters [J].
Bouillon, A ;
Lancelot, JC ;
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 2002, 58 (17) :3323-3328
[6]   Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters [J].
Bouillon, A ;
Lancelot, JC ;
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 2002, 58 (14) :2885-2890
[7]  
BRYDOWNA W, 1934, ROCZNIKI CHEM, V14, P304
[8]   Synthesis of ortho-cyanopyridylboronic acids and esters toward cyano-functionalized bipyridines [J].
Cailly, T ;
Fabis, F ;
Bouillon, A ;
Lemaître, S ;
Sopkova, J ;
de Santos, O ;
Rault, S .
SYNLETT, 2006, (01) :53-56
[9]   A new, direct, and efficient synthesis of benzonaphthyridin-5-ones [J].
Cailly, Thomas ;
Fabis, Frederic ;
Rault, Sylvain .
TETRAHEDRON, 2006, 62 (25) :5862-5867
[10]   SUBSTITUTED 1,10-PHENANTHROLINES .11. AZA DERIVATIVES [J].
CASE, FH ;
BRENNAN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (23) :6297-6301