The modified-Mannich reaction: Conversion of arylboronic acids and subsequent coupling with paraformaldehyde and amines toward the one-pot synthesis of Mannich bases and benzoxazines

作者: Juan Liu , Gaoqing Yuan

DOI: 10.1016/J.TETLET.2017.02.081

关键词:

摘要: Abstract A modified Mannich reaction has been developed for the synthesis of bases and benzoxazines via oxidative hydroxylation arylboronic acids subsequent coupling with paraformaldehyde amines in one pot. This is easily carried out to afford target products good excellent yields tolerates a variety functional groups.

参考文章(45)
Surabhi Gupta, Priyanka Chaudhary, Lavudi Seva, Shahulhameed Sabiah, Jeyakumar Kandasamy, Bio-based green solvent for the catalyst free oxidation of arylboronic acids into phenols RSC Advances. ,vol. 5, pp. 89133- 89138 ,(2015) , 10.1039/C5RA18080E
Pranjal Gogoi, Pranjal Bezboruah, Junali Gogoi, Romesh C. Boruah, ipso‐Hydroxylation of Arylboronic Acids and Boronate Esters by Using Sodium Chlorite as an Oxidant in Water European Journal of Organic Chemistry. ,vol. 2013, pp. 7291- 7294 ,(2013) , 10.1002/EJOC.201301228
Yanxia Zhang, Jianwei Han, Zhen-Jiang Liu, None, Diaryliodonium salts as efficient Lewis acid catalysts for direct three component Mannich reactions RSC Advances. ,vol. 5, pp. 25485- 25488 ,(2015) , 10.1039/C5RA00209E
Qi-Xiang Guo, Hua Liu, Chang Guo, Shi-Wei Luo, Yi Gu, Liu-Zhu Gong, Chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction. Journal of the American Chemical Society. ,vol. 129, pp. 3790- 3791 ,(2007) , 10.1021/JA068236B
Hiroyasu Takahashi, Nobuyuki Kashiwa, Yuichi Hashimoto, Kazuo Nagasawa, Novel Mannich-type nucleophilic substitution reaction with tertiary aromatic amines Tetrahedron Letters. ,vol. 43, pp. 2935- 2938 ,(2002) , 10.1016/S0040-4039(02)00447-1
S.A. Monti, W.O. Johnson, Position selective mannich reactions of some 5- and 6-hydroxyindoles Tetrahedron. ,vol. 26, pp. 3685- 3694 ,(1970) , 10.1016/S0040-4020(01)92947-3
Chen Zhu, Rui Wang, J. R. Falck, Mild and Rapid Hydroxylation of Aryl/Heteroaryl Boronic Acids and Boronate Esters with N-Oxides Organic Letters. ,vol. 14, pp. 3494- 3497 ,(2012) , 10.1021/OL301463C
Tomoaki Hamada, Kei Manabe, Shū Kobayashi, Enantio- and diastereoselective, stereospecific mannich-type reactions in water. Journal of the American Chemical Society. ,vol. 126, pp. 7768- 7769 ,(2004) , 10.1021/JA048607T
Augusto Rivera, Rodolfo Quevedo, Solvent-free Mannich-type reaction of tetraazatricyclododecane (TATD) with phenols Tetrahedron Letters. ,vol. 54, pp. 1416- 1420 ,(2013) , 10.1016/J.TETLET.2012.12.116