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
[21]   Reaction of bromomethylazoles and tosylmethyl isocyanide. A novel heterocyclization method for the synthesis of the core of marine alkaloids variolins and related azolopyrimidines [J].
Mendiola, J ;
Baeza, A ;
Alvarez-Builla, J ;
Vaquero, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :4974-4983
[22]   Reaction of 2-bromomethylazoles and TosMIC: A domino process to azolopyrimidines. Synthesis of core tricycle of the variolins alkaloids [J].
Mendiola, J ;
Minguez, JM ;
Alvarez-Builla, J ;
Vaquero, JJ .
ORGANIC LETTERS, 2000, 2 (21) :3253-3256
[23]   Pyrrolodiazines.: 5.: Synthesis, structure, and chemistry of pyrrolo[1,2-c]pyrimidine.: Dipolar cycloaddition of pyrrolo[1,2-c]pyrimidinium ylides [J].
Minguez, JM ;
Vaquero, JJ ;
Alvarez-Builla, J ;
Castaño, O ;
Andrés, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7788-7801
[24]   Carbodiimide-mediated preparation of the tricyclic pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine ring system and its application to the synthesis of the potent antitumoral marine alkaloid variolin B and analog [J].
Molina, P ;
Fresneda, PM ;
Delgado, S .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :489-499
[25]   Synthesis of the potent antitumoral marine alkaloid variolin B [J].
Molina, P ;
Fresneda, PM ;
Delgado, S ;
Bleda, JA .
TETRAHEDRON LETTERS, 2002, 43 (06) :1005-1007
[26]  
OJIJNSMA T, 1973, SYNTHETIC COMMUN, V3, P1
[27]   ALKALOIDS FROM THE ANTARCTIC SPONGE KIRKPATRICKIA-VARIALOSA .1. VARIOLIN-B, A NEW ANTITUMOR AND ANTIVIRAL COMPOUND [J].
PERRY, NB ;
ETTOUATI, L ;
LITAUDON, M ;
BLUNT, JW ;
MUNRO, MHG ;
PARKIN, S ;
HOPE, H .
TETRAHEDRON, 1994, 50 (13) :3987-3992
[28]   Variolin B and its derivate deoxy-variolin B: New marine natural compounds with cyclin-dependent kinase inhibitor activity [J].
Simone, M ;
Erba, E ;
Damia, G ;
Vikhanskaya, F ;
Di Francesco, AM ;
Riccardi, R ;
Bailly, C ;
Cuevas, C ;
Sousa-Faro, JMF ;
D'Incalci, M .
EUROPEAN JOURNAL OF CANCER, 2005, 41 (15) :2366-2377
[29]   ALKALOIDS FROM THE ANTARCTIC SPONGE KIRKPATRICKIA-VARIALOSA .2. VARIOLIN-A AND N(3')-METHYL TETRAHYDROVARIOLIN-B [J].
TRIMURTULU, G ;
FAULKNER, DJ ;
PERRY, NB ;
ETTOUATI, L ;
LITAUDON, M ;
BLUNT, JW ;
MUNRO, MHG ;
JAMESON, GB .
TETRAHEDRON, 1994, 50 (13) :3993-4000
[30]   Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates [J].
Wolfe, JP ;
Tomori, H ;
Sadighi, JP ;
Yin, JJ ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (04) :1158-1174