The mechanism of unexpected reduction of dimethyl pyridine-2,3-dicarboxylate to l,2,3,4-tetrahydrofuro[3,4-b]-pyridin-5(7H)-one with sodium borohydride
The mechanism of unexpected reduction of dimethyl pyridine-2,3-dicarboxylate to l,2,3,4-tetrahydrofuro[3,4-b]- pyridin-5(7H)-one with sodium borohydride
摘要
An unexpected reduction of dimethyl pyridine-2,3-dicarboxylate to 1,2,3,4-tetrahydrofuro[3,4-b]pyridin-5(7H)-one with sodium borohydride in ethanol and tetrahydrofuran, respectively, is described, a hypothetic mechanism for the unusual reductive product is proposed.
An unexpected reduction of dimethyl pyridine-2,3-dicarboxylate to 1,2,3,4-tetrahydrofuro[3,4-b]pyridin-5(7H)-one with sodium borohydride in ethanol and tetrahydrofuran, respectively, is described, a hypothetic mechanism for the unusual reductive product is proposed.
参考文献13
-
1M. Periasamy, M. Thirumalaikumar, J. Organomet. Chem. 609 (2000) 137.
-
2A.B.S. Prasad, J.V.B. Kanth, M. Periassamy, Tetrahedron 48 (1992) 4623.
-
3T. Yamakawa, M. Masaki, H. Nohira, Bull. Chem. Soc. Jpn. 64 (1991) 2730.
-
4N. Boechat, J.C.S. da Costa, J. de Souza Mendonca, et al. Tetrahedron Lett. 45 (2004) 6021.
-
5N. Boechat, J.C.S. da Costa, J. de Souza Mendonca, et al. Synth. Commun. 35 (2005) 3187.
-
6K. Yoshiizumi, M. Yamamoto, T. Miyasaka, et al. Bioorg. Med. Chem. 11 (2003) 433.
-
7Z. Tang, J. Mayrargue, M. Alami, Synth. Commun. 37 (2007) 3367.
-
8H. Sakagami, T. Kamikubo, K. Ogasawara, Chem. Commun. (1996) 1433.
-
9H. Sakagami, K. Ogasawara, Synthesis (2000) 521.
-
10C.Y. Cheng, L.W. Hsin, J.P. Liou, Tetrahedron 52 (1996) 10935.
-
1DanQianXU ShuPingLUO BaoYouLIU ZhenYuanXU YinChuSHEN.Ambient Ionic Liquids Used in the Reduction of Aldehydes and Ketones[J].Chinese Chemical Letters,2004,15(6):643-645. 被引量:3
-
2刘保霞,郑昕,刘新明,韦秀华,孙雨安.5-降冰片烯-2,3-二羧酸二甲酯的合成与表征[J].十堰职业技术学院学报,2007,20(5):87-88. 被引量:1
-
3那玉贤,许肖龙.顺反1,2—环丙烷二羧酸二甲酯及其衍生物的色谱分析[J].分析化学,1989,17(5):459-462.
-
4Erler,W.,吴国强.用氯化锡(II)和氢硼化钠汞齐化技术测定汞[J].国外分析仪器技术与应用,1989(2):46-47.
-
5林旭群,李树军.三环[5,2,1,0^(2,6)]癸-3-烯-8,9-二羧酸二甲酯的合成[J].广州化学,1995(4):47-50.
-
6Hong Bin ZHOU,Xin De FNEG,Qi Feng ZHOU.THE UNUSUAL REDUCTION OF SOME AROMATIC ALDEHYDES BY SODIUM BOROHYDRIDE[J].Chinese Chemical Letters,1991,2(8):609-610.
-
7郭向广,吴小园,张其凯,杨文斌,林琅,余荣民,卢灿忠.A Y(Ⅲ)-organic Coordination Polymer Constructed from 2-(Pyridine-4-yl)-1H-imidazole-4,5-dicarboxylate and Oxalate Ligands: Structure and Luminescent Property[J].Chinese Journal of Structural Chemistry,2013,32(1):57-62.
-
8Foad Kazemi,Ali Reza Kiasat,Ebrahim Sarvestani.Practical reduction of imines by NaBH_4/alumina under solvent-free conditions:An efficient route to secondary amine[J].Chinese Chemical Letters,2008,19(10):1167-1170.
-
9YuXIA,XiangShuXIAO,等.The Unexpected Reductive Products of δ-Alkoxyenal by Sodium Borohydride in Methanol with A Trace of Magnesium Methoxide[J].Chinese Chemical Letters,2002,13(9):809-810.
-
10裴伟伟,裴坚,淳炯,叶秀林.芝麻素类型木脂素的合成研究Ⅳ2-苯基呋喃3,4-二羧酸二甲脂与格氏试剂反应的研究[J].北京大学学报(自然科学版),1994,30(2):173-176.