Selective palladium-catalyzed amination of the heterocyclic core of variolins

被引:14
作者
Baeza, Alejandro [1 ]
Burgos, Carolina [1 ]
Alvarez-Builla, Julio [1 ]
Vaquero, Juan J. [1 ]
机构
[1] Univ Alcala de Henares, Dept Quim Organ, Madrid, Spain
关键词
pyrido[3 ',3 ': 4,5]pyrrolo[1,2-c]pyrimidine; N-tosylmethyl dichloroformimide; amination; palladium-catalyzed; variolins; SPONGE KIRKPATRICKIA-VARIALOSA; TOSYLMETHYL ISOCYANIDE; ALKALOIDS VARIOLINS; ARYL HALIDES; MERIDIANINS; DERIVATIVES; ARYLAMINES; OXAZOLES; SYSTEM;
D O I
10.1016/j.tetlet.2007.02.011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and selective palladium-catalyzed amination of the pyrido[3',3':4,5]pyrrolo[1,2-c]pyrimidine nucleus, the heterocyclic core of the variolin alkaloids, is described. The method allows the introduction of amino and aryl- and alkyjamino substituents on the C9 position in advanced precursors of variolin B and deoxyvariolin. (c) 2007 Published by Elsevier Ltd.
引用
收藏
页码:2597 / 2601
页数:5
相关论文
共 31 条
[1]   Total syntheses of variolin B and deoxyvariolin B [J].
Ahaidar, A ;
Fernández, D ;
Danelón, G ;
Cuevas, C ;
Manzanares, I ;
Albericio, F ;
Joule, JA ;
Alvarez, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10020-10029
[2]   Synthesis of variolin B [J].
Ahaidar, A ;
Fernández, D ;
Pérez, O ;
Danelón, G ;
Cuevas, C ;
Manzanares, I ;
Albericio, F ;
Joule, JA ;
Alvarez, M .
TETRAHEDRON LETTERS, 2003, 44 (33) :6191-6194
[3]   Synthesis of deoxyvariolin B [J].
Alvarez, M ;
Fernández, D ;
Joule, JA .
TETRAHEDRON LETTERS, 2001, 42 (02) :315-317
[4]   Concise total syntheses of variolin B and deoxyvariolin B [J].
Anderson, RJ ;
Hill, JB ;
Morris, JC .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6204-6212
[5]   Total synthesis of variolin B [J].
Anderson, RJ ;
Morris, JC .
TETRAHEDRON LETTERS, 2001, 42 (49) :8697-8699
[6]   Studies toward the total synthesis of the variolins: rapid entry to the core structure [J].
Anderson, RJ ;
Morris, JC .
TETRAHEDRON LETTERS, 2001, 42 (02) :311-313
[7]   Heterocyclizations with tosylmethyl isocyanide derivatives. A new approach to substituted azolopyrimidines [J].
Baeza, A ;
Mendiola, J ;
Burgos, C ;
Alvarez-Builla, J ;
Vaquero, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) :4879-4882
[8]   Synthesis of polyheterocyclic nitrogen-containing marine natural products [J].
Fernández, D ;
Ahaidar, A ;
Danelón, G ;
Cironi, P ;
Marfil, M ;
Pérez, O ;
Cuevas, C ;
Albericio, F ;
Joule, JA ;
Alvarez, M .
MONATSHEFTE FUR CHEMIE, 2004, 135 (06) :615-627
[9]   Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B [J].
Fresneda, PM ;
Delgado, S ;
Francesch, A ;
Manzanares, I ;
Cuevas, C ;
Molina, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (03) :1217-1221
[10]   Synthetic studies towards the 2-aminopyrimidine alkaloids variolins and meridianins from marine origin [J].
Fresneda, PM ;
Molina, P ;
Delgado, S ;
Bleda, JA .
TETRAHEDRON LETTERS, 2000, 41 (24) :4777-4780