Palladium-catalyzed intramolecular C-arylation of benzylic carbon: synthesis of 3-benzoxazolylisoindolinones by a sequence of Ugi-4CR/postfunctionalization.

作者: Angela Salcedo , Luc Neuville , Jieping Zhu

DOI: 10.1021/JO800266Y

关键词:

摘要: Submitting Ugi-adduct 4 to two consecutive metal-catalyzed intramolecular reactions, namely copper-catalyzed O-arylation and palladium-catalyzed C-arylation of benzylic carbon developed in the course this study, affords benzoxazolylisoindolinones good excellent yields.

参考文章(67)
Shoukou Lee, Chihiro Shinji, Kiyoshi Ogura, Motomu Shimizu, Satoko Maeda, Mayumi Sato, Minoru Yoshida, Yuichi Hashimoto, Hiroyuki Miyachi, Design, synthesis, and evaluation of isoindolinone-hydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors Bioorganic & Medicinal Chemistry Letters. ,vol. 17, pp. 4895- 4900 ,(2007) , 10.1016/J.BMCL.2007.06.038
Pierre Cristau, Jean-Pierre Vors, Jieping Zhu, A Rapid Access to Biaryl Ether Containing Macrocycles by Pairwise Use of Ugi 4CR and Intramolecular SNAr-Based Cycloetherification Organic Letters. ,vol. 3, pp. 4079- 4082 ,(2001) , 10.1021/OL0168420
Gang Zhao, Xiaowen Sun, Hugues Bienaymé, Jieping Zhu, Activation of a terminal carboxylic acid by an internal oxazole: a novel synthesis of macrocyclodepsipeptide. Journal of the American Chemical Society. ,vol. 123, pp. 6700- 6701 ,(2001) , 10.1021/JA015854D
Stefano Marcaccini, Tomás Torroba, The use of the Ugi four-component condensation Nature Protocols. ,vol. 2, pp. 632- 639 ,(2007) , 10.1038/NPROT.2007.71
Jonathan Clayden, Lluís Vallverdú, Madeleine Helliwell, Conformational communication between the Ar-CO and Ar-N axes in 2,2'-disubstituted benzanilides and their derivatives. Organic and Biomolecular Chemistry. ,vol. 4, pp. 2106- 2118 ,(2006) , 10.1039/B602912D
Shu-Ting Huang, I-Jen Hsei, Chinpiao Chen, Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles. Bioorganic & Medicinal Chemistry. ,vol. 14, pp. 6106- 6119 ,(2006) , 10.1016/J.BMC.2006.05.007
Armelle Ouali, Marc Taillefer, Jean-F. Spindler, Anny Jutand, Precatalysts involved in copper-catalyzed arylations of nucleophiles Organometallics. ,vol. 26, pp. 65- 74 ,(2007) , 10.1021/OM060706N
Dawei Ma, Yongda Zhang, Jiangchao Yao, Shihui Wu, Fenggang Tao, Accelerating effect induced by the structure of αamino acid in the copper-catalyzed coupling reaction of aryl halides with α-amino acids. Synthesis of benzolactam-V8 Journal of the American Chemical Society. ,vol. 120, pp. 12459- 12467 ,(1998) , 10.1021/JA981662F
Barbara Beck, Gregor Larbig, Beatrice Mejat, Marina Magnin-Lachaux, Anne Picard, Eberhardt Herdtweck, Alexander Dömling, Short and diverse route toward complex natural product-like macrocycles. Organic Letters. ,vol. 5, pp. 1047- 1050 ,(2003) , 10.1021/OL034077E