[1]沈美华,卢小龙,刘雅婷,等.取代1,2-二氢吡嗪化合物的合成[J].常州大学学报(自然科学版),2017,(01):56-61.[doi:doi:10.3969/j.issn.2095-0411.2017.01.010]
　SHEN Meihua,LU Xiaolong,LIU Yating,et al.Synthesis of Substituted 1,2-Dihydropyrazines[J].Journal of Changzhou University(Natural Science Edition),2017,(01):56-61.[doi:doi:10.3969/j.issn.2095-0411.2017.01.010]
点击复制

取代1,2-二氢吡嗪化合物的合成()
分享到：

常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
期数:
2017年01期
页码:
56-61
栏目:
生物医学工程
出版日期:
2017-01-28

文章信息/Info

Title:
Synthesis of Substituted 1,2-Dihydropyrazines
作者:
沈美华; 卢小龙; 刘雅婷; 王清霞
常州大学 制药与生命科学学院,江苏 常州 213164
Author(s):
SHEN Meihua;  LU Xiaolong;  LIU Yating;  WANG Qingxia
School of Pharmaceutical Engineering & Life Science, Changzhou University,Changzhou 213164, China
关键词:
1-磺酰基三氮唑;  2H-氮丙啶;  N-磺酰基-1; 2-二氢吡嗪;  合成
Keywords:
1-sulfonyl triazole;  2H-azirine;  N-sulfonyl-1; 2-dihydropyrazine;  synthesis
分类号:
O 626.4
DOI:
doi:10.3969/j.issn.2095-0411.2017.01.010
文献标志码:
A
摘要:
研究了1-磺酰基三氮唑在二聚醋酸铑催化下和2H-氮丙啶发生反应生成一系列苯基取代N-磺酰基-1,2-二氢吡嗪化合物的合成方法。考察了催化剂和溶剂对产物产率的影响。化合物结构经1H NMR和13C NMR鉴定和表征。该反应为二氢吡嗪化合物的合成提供了一种新颖的途径。
Abstract:
The method for the synthesis of a series of phenyl-substituted N-sulfonyl-1,2-dihyropyrazines via the reaction of 1-sulfonyl triazoles with 2H-azirines catalyzed by Rh2(OAc)4 has been realized. The effect of catalysts and solvents on the yield of products has been evaluated. The structures of target products have been identified by 1H NMR and 13C NMR. This reaction offered a novel approach for the synthesis of dihydropyrazines.

参考文献/References:

[1]SIT S Y, HUANG Y, ANTAL-ZIMANYI,et al. Novel dihydropyrazine analogues as NPY antagonists[J]. Bioorg Med Chem Lett, 2002, 12(3): 337-340.
[2]ITO S, TAKECHI S, NAKAHARA K, et al.Phenyl-substituted dihydropyrazines with DNA strand-breakage activity[J]. Chem Pharm Bull, 2010, 58(6): 825-828.
[3]HORTON D A, BOUME G T, SMYTHE M L.The combinatorial synthesis of bicyclic privileged structures or privileged substructures[J]. Chem Rev, 2003, 103(3): 893-930.
[4]VIETH M, SIEGEL M G, HIGGS R E, et al.Characteristic physical properties and structural fragments of marketed oral drugs[J]. J Med Chem, 2004, 47(1): 224-232.
[5]WILLIAMS A L, HILAIRE V R, LEE T.Regioselective reduction of 3-substituted N-acylpyrazinium salts toward the synthesis of 1,2-dihydropyrazines[J]. J Org Chem, 2012, 77(8): 4097-4102.
[6]FAN L, CHEN W, QIAN C.YbCl3-catalyzed one-pot synthesis of dihydropyrazines, piperazines, and pyrazines[J]. Tetrahedron Lett, 2013, 54(3): 231-234.
[7]XU H D, XU K, JIA Z H, et al.Substituent enabled divergent synthesis of N-heterocycles: a metal carbene approach involving intramolecular carbene interception[J]. Asian J Org Chem 2014, 3(11): 1154-1158.
[8]SHEN M H, PAN Y P, JIA Z H, et al. An efficient approach to 1,2,3-trisubstituted indole via rhodium catalyzed carbene Csp3-H bond insertion[J]. Org Biomol Chem, 2015, 13(17): 4851-4854.
[9]石传理. 过渡金属催化合成含氮杂环化合物的研究[D]. 温州:温州大学,2012.
[10]吴彩虹. 过渡金属催化含氮杂环化合物合成机理的理论研究[D]. 广州:暨南大学,2014.
[11]HOMEFF T, CHUPRAKOV S, CHERNYAK N, et al.Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles[J]. J Am Chem Soc, 2008, 130(45): 14972-14974.
[12]KHLEBNIKOV A F, NOVIKOV M S.Recent advances in 2H-azirine chemistry[J]. Tetrahedron, 2013, 69(16): 3363-3401.
[13]XU H D, ZHOU H, PAN Y P, et al. Stereoselective synthesis of polycycles containing an aziridine group: Intramolecular aza-Diels-Alder reactions of unactivated 2H-azirines with unactivated dienes[J]. Angew Chem Int Ed, 2016, 55(7): 2540-2544.
[14]RAUSHEL J, FOKIN V V. Efficient synthesis of 1-sulfonyl-1,2,3-triazoles[J]. Org Lett, 2010, 12(21): 4952-4955.
[15]XING Y, SHENG G, WAMG J, et al. Preparation of triazoloindoles via tandem copper catalysis and their utility as α-imino rhodium carbene precursors[J]. Org Lett, 2014, 16(4): 1244-1247.
[16]DING H, HONG S, ZHANG N. Rhodium(II)-catalyzed transannulation of 1-sulfonyl-1,2,3-triazoles with 2H-azirines: a new method to dihydropyrazines[J]. Tetrahedron Lett, 2015, 56(3): 507-510.
[17]XUAN J, XIA X D, XIAO W J, et al. Visible-light-inducedf formal[3+2]Cycloaddition for pyrrole synthesis under metal-free conditions[J].Angew Chem Int Ed, 2014, 53(22): 5653-5656.
[18]WANG Y, LEI X, TANG Y. Rh(II)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: switchable reactivity of Rh-azavinylcarbene as[2C]-or Aza-[3C]-synthon[J]. Chem Commun, 2015, 51(21): 4507-4510.

备注/Memo

备注/Memo:
收稿日期:2016-06-02。
基金项目:国家自然科学基金资助项目(21402014)。
作者简介:沈美华(1977—),女,江苏苏州人,博士,副教授,主要从事有机合成化学研究。
更新日期/Last Update: 2017-02-10