研究简报

腐殖酸作用下Strecker反应快速高效合成α-氨基腈

  • 席敏 ,
  • 段超 ,
  • 迟捷 ,
  • 付甜 ,
  • 苏小龙 ,
  • 王宏社
展开
  • 宝鸡文理学院化学化工学院 陕西省植物化学重点实验室 陕西宝鸡 721013

收稿日期: 2023-01-29

  修回日期: 2023-03-26

  网络出版日期: 2023-05-11

基金资助

国家自然科学基金(51902004); 陕西省自然科学基金(2020KW-041)

An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid

  • Min Xi ,
  • Chao Duan ,
  • Jie Chi ,
  • Tian Fu ,
  • Xiaolong Su ,
  • Hongshe Wang
Expand
  • Shaanxi Key Laboratory for Phytochemistry, Department of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013

Received date: 2023-01-29

  Revised date: 2023-03-26

  Online published: 2023-05-11

Supported by

National Natural Science Foundation of China(51902004); Natural Science Foundation of Shaanxi Province(2020KW-041)

摘要

以腐殖酸为催化剂, 在室温无溶剂条件下, 通过醛(酮)、胺和三甲基硅氰(TMSCN)的一锅三组分Strecker反应, 绿色高效合成了α-氨基腈. 该法具有产率高、无需金属催化剂、反应时间短、反应条件温和、操作简便以及催化剂绿色并可重复使用等优点.

本文引用格式

席敏 , 段超 , 迟捷 , 付甜 , 苏小龙 , 王宏社 . 腐殖酸作用下Strecker反应快速高效合成α-氨基腈[J]. 有机化学, 2023 , 43(9) : 3312 -3318 . DOI: 10.6023/cjoc202301024

Abstract

An efficient one pot three-component Strecker reaction for the green synthesis of α-aminonitriles from carbonyl compounds, amines and trimethylsilyl cyanide (TMSCN) in the presence of a catalytic amount of humic acid catalyst under solvent-free conditions at room temperature has been developed. This methodology has advantages of high yield, no need for metal catalysts, short reaction time, mild reaction conditions, simple operation, green and reusable catalyst.

参考文献

[1]
Enders D.; Shilvock J. P. Chem. Soc. Rev. 2000, 29, 359.
[2]
(a) Wagner A.; Ofial A. R. J. Org. Chem. 2015, 80, 2848.
[2]
(b) Echevarria I.; Vaquero M.; Quesada R.; Espino G. Inorg. Chem. Front. 2020, 7, 3092.
[2]
(c) He W.-B.; Tang L.-L.; Jiang J.; Li X.; Xu X.; Yang T.-B.; He W.-M. Molecules 2023, 28, 1397.
[2]
(d) Gui Q.-W.; He X.; Wang W.; Zhou H.; Dong Y.; Wang N.; Tang J.-X.; Cao Z.; He W.-M. Green Chem. 2020, 22, 118.
[2]
(e) Gui Q.-W.; Teng F.; Ying S.-N.; Liu Y.; Guo T.; Tang J.-X.; Chen J.-Y.; Cao Z.; He W.-M. Chin. Chem. Lett. 2020, 31, 3241.
[3]
(a) Wang J.; Liu X.; Feng X. Chem. Rev. 2011, 111, 6947.
[3]
(b) Negru M.; Schollmeyer D.; Kunz H. Angew. Chem., Int. Ed. 2007, 46, 9339.
[3]
(c) Wang J.; Hu X.; Jiang J.; Gou S.; Huang X.; Liu X.; Feng X. Angew. Chem., Int. Ed. 2007, 46, 8468.
[3]
(d) Miyagawa S.; Yoshimura K.; Yamazaki Y.; Takamatsu N.; Kuraishi T.; Aiba S.; Tokunaga Y.; Kawasaki T. Angew. Chem., Int. Ed. 2017, 56, 1055.
[3]
(e) Ma H.-C.; Chen G.-J.; Huang F.; Dong Y.-B. J. Am. Chem. Soc. 2020, 142, 12574.
[3]
(f) Abell J. P.; Yamamoto H. J. Am. Chem. Soc. 2009, 131, 15118.
[3]
(g) Masumoto S.; Usuda H.; Suzuki M.; Kanai M.; Shibasaki M. J. Am. Chem. Soc. 2003, 125, 5634.
[4]
Harusawa S.; Hmada Y.; Shiori T. Tetrahedron Lett. 1979, 20, 4663.
[5]
Nakamura S.; Sato N.; Sugimoto M.; Toru T. Tetrahedron: Asymmetry 2004, 15, 1513.
[6]
Vachal P.; Jacobsen E. N. J. Am. Chem. Soc. 2002, 124, 10012.
[7]
Li Z.; Ma Y.; Xu J.; Shi J.; Cai H. Tetrahedron Lett. 2010, 51, 3922.
[8]
Cruz-Acosta F.; Santos-Exposito A.; Armas P.; Garcia-Tellado F. Chem. Commun. 2009, 45, 6839.
[9]
Sipos S.; Jablonkai I. Tetrahedron Lett. 2009, 50, 1844.
[10]
Abell J. P.; Yamamoto H. J. Am. Chem. Soc. 2009, 131, 15118.
[11]
Khalaf E.; Alameri A. A.; Malviya J.; Kumar T. C. A.; Altalbawy F. M. A.; Alfilh R. H. C.; KazemneJadi M. Catal. Lett. 2022, 152, 3317.
[12]
Hernandez J. G.; Turberg M.; Schiffers I.; Bolm C. Chem.-Eur. J. 2016, 22, 14513.
[13]
Baghery S.; Zolfigol M. A.; Schirhagl R.; Hasani M.; Stuart M. C. A.; Nagl A. Appl. Organomet. Chem. 2017, 31, 3883.
[14]
Mousavi-Mashhadi S. A.; Shiri A. Mol. Divers. 2022, 26, 3463.
[15]
Kaur G.; Shamim M.; BhardwaJ V.; Gupta V. K.; BanerJee B. Synth. Commun. 2020, 50, 1545.
[16]
MoJtahedi M. M.; Abaee M. S.; Alishiri T. Tetrahedron Lett. 2009, 50, 2322.
[17]
Pasha M. A.; NanJundaswamy H. M.; Jayashankara V. P. Synth. Commun. 2007, 37, 4371.
[18]
(a) Eslami M.; Dekamin M. G.; Motlagh L.; Maleki A. Green Chem. Lett. Rev. 2018, 11, 36.
[18]
(b) Kouznetsov V. V.; Hernandez J. G. RSC Adv. 2022, 12, 20807.
[19]
Royer L.; De S. K.; Gibbs R. A. Tetrahedron Lett. 2005, 46, 4595.
[20]
(a) Dekamin M. G.; Azimoshan M.; Ramezani L. Green Chem. 2013, 15, 811.
[20]
(b) Das S.; Kumar R.; Devadkar A.; Panda T. K. Asian J. Org. Chem. 2020, 9, 1217.
[21]
Rahmati M.; Ghafuri H. Res. Chem. Intermed. 2021, 47, 1489.
[22]
Verma K.; Sharma A.; Badru R. Curr. Res. Green Sustainable Chem. 2021, 4, 100060.
[23]
Kaur B.; Chand S.; Malik A. K. J. Clean. Prod. 2019, 234, 329.
[24]
Nasseri M. A.; Ramezani-Moghadam S.; KazemneJadi M.; Allahresani A. Res. Chem. Intermed. 2020, 46, 4233.
[25]
Zareyee D.; Rad A. S.; Ataei Z. Appl. Organomet. Chem. 2018, 32, 4422.
[26]
Fatahi H.; Jafarzadeh M.; Pourmanouchehri Z. J. Heterocycl. Chem. 2019, 56, 2090.
[27]
Wu J.; Chen W.; Luo M.; He X.; Li Z. Chin. J. Org. Chem. 2010, 30, 1497. (in Chinese)
[27]
(邬继荣, 陈巍峰, 罗蒙贤, 贺小林, 李志芳, 有机化学, 2010, 30, 1497.)
[28]
Maleki A.; Azadegan S.; Rahimi J. Appl. Organomet. Chem. 2019, 33, 4810.
[29]
(a) Reinares-Fisac D.; Aguirre-Diaz L. M.; Iglesias M. J. Am. Chem. Soc. 2016, 138, 9089.
[29]
(b) Gandhi S.; Sharma V.; Koul I. S.; Mandal S. K. Catal. Lett. 2022, 152, 3558.
[29]
(c) Gomez-Oliveira E. P.; Mendez N.; Iglesias M.; Gutierrez- Puebla E.; Aguirre-Diaz L. M.; Monge M. A. Inorg. Chem. 2022, 61, 7523.
[29]
(d) Ramsperger C. A.; Tufts N. Q.; Yadav A. K.; Lessard J. M.; Stylianou K. C. ACS Appl. Mater. Interfaces 2022, 14, 49957.
[29]
(e) Gupta V.; Mandal S. K. Inorg. Chem. 2019, 58, 3219.
[29]
(f) Gupta V.; Mandal S. K. Inorg. Chem. 2020, 59, 4273.
[29]
(g) Khan S.; Markad D.; Mandal S. K. Inorg. Chem. 2023, 62, 275.
[29]
(h) Sachan S. K.; Anantharaman G. Inorg. Chem. 2021, 60, 9238.
[30]
Li X.-T.; Zou J.; Wang T.-H.; Ma H.-C.; Chen G.-J.; Dong Y.-B. J. Am. Chem. Soc. 2020, 142, 6521.
[31]
(a) Song H.-Y.; Liu M.-Y.; Huang J.; Wang D.; Jiang J.; Chen J.-Y.; Yang T.-B.; He W.-M. J. Org. Chem. 2023, 88, 2288.
[31]
(b) He W.-B.; Zhao S.-J.; Chen J.-Y.; Jiang J.; Chen X.; Xu X.; He W.-M. Chin. Chem. Lett. 2023, 34, 107640.
[31]
(c) Chen J.-Y.; Li H.-X.; Mu S.-Y.; Song H.-Y.; Wu Z.-L.; Yang T.-B.; Jiang J.; He W.-M. Org. Biomol. Chem. 2022, 20, 8501.
[31]
(d) Gui Q.-W.; Wang B.-B.; Zhu S.; Li F.-L.; Zhu M.-X.; Yi M.; Yu J.-L.; Wu Z.-L.; He W.-M. Green Chem. 2021, 23, 4430.
[32]
Han B.; He X. H.; Liu Y. Q.; He G.; Peng C.; Li J. L. Chem. Soc. Rev. 2021, 50, 1522.
[33]
(a) Mitra B.; Ghosh P. ChemistrySelect 2021, 6, 68.
[33]
(b) Wei Z.; Li J.; Wang Z.; Li P.; Wang Y. Chin. J. Org. Chem. 2017, 37, 1835. (in Chinese)
[33]
(魏振中, 李江飞, 王泽云, 李品华, 王永秋, 有机化学, 2017, 37, 1835.)
[34]
Zhang Y.; Han M. J. Chem. Res. 2011, 35, 568.
[35]
Chaturvedi D.; Chaturvedi A. K.; Mishra N.; Mishra V. Tetrahedron Lett. 2012, 53, 5398.
[36]
MaJhi A.; Kim S. S.; Kadam S. T. J. Organomet. Chem. 2008, 22, 705.
[37]
Reddy B. M.; Thirupathi B.; Patil M. K. J. Mol. Catal. A: Chem. 2009, 307, 154.
[38]
Maleki A.; Akhlaghi E.; Paydar R. Appl. Organomet. Chem. 2016, 30, 382.
文章导航

/