REVIEWS

New Progress of Fully Continuous Flow Reaction Technologies in Pharmaceutical Synthesis (2019~2022)

  • Kangbo Feng ,
  • Jiong Chen ,
  • Shuangxi Gu ,
  • Haifeng Wang ,
  • Fen'er Chen
Expand
  • a Key Laboratory for Green Chemical Process of Ministry of Education, School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430205
    b Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205
    c Hubei Key Laboratory of Novel Reactor and Green Chemical Technology, Wuhan Institute of Technology, Wuhan 430205
    d Department of Chemistry, Fudan University, Shanghai 200433
* Corresponding authors. E-mail: ;

Received date: 2023-07-09

  Revised date: 2023-09-16

  Online published: 2023-09-28

Supported by

National Natural Science Foundation of China(22377097); National Natural Science Foundation of China(21877087); Natural Science Foundation of Hubei Province(2021CFB556); Natural Science Foundation of Hubei Province(2022CFB156); Key Laboratory for Green Chemical Process of Ministry of Education Open Fund(GCP20200201); Hubei Key Laboratory of Novel Reactor and Green Chemical Technology (Wuhan Institute of Technology) Open Fund(40201002)

Abstract

Continuous flow chemistry is an emerging technology in the chemical pharmaceutical industry. Compared with the traditional batch kettle reaction, continuous flow reaction has the advantages of rapid mass and heat transfer, improves the controllability and safety of the reaction process, and can also integrate the online analysis and purification steps into the flexible operation sequence. The new progress of continuous flow reaction technology in the continuous synthesis process from starting raw material to final active pharmaceutical ingredient (API) from 2019 to 2022 is introduced. Starting from the flow chart of continuous flow reaction, the preparation process and technical advantages of continuous flow reaction are described. At the same time, it is pointed out that the fully continuous flow reaction technology still has some challenges in the process connection and coupling treatment of each single step synthesis transformation, which needs to be further improved.

Cite this article

Kangbo Feng , Jiong Chen , Shuangxi Gu , Haifeng Wang , Fen'er Chen . New Progress of Fully Continuous Flow Reaction Technologies in Pharmaceutical Synthesis (2019~2022)[J]. Chinese Journal of Organic Chemistry, 2024 , 44(2) : 378 -397 . DOI: 10.6023/cjoc202307005

References

[1]
Mcquade, D. T.; Seeberger, P. H. J. Org. Chem. 2013, 78, 6384.
[2]
Plutschack, M. B.; Pieber, B.; Gilmore, K.; Seeberger, P. H. Chem. Rev. 2017, 117, 11796.
[3]
Adamo, A.; Beingessner, R. L.; Behnam, M.; Chen, J.; Jamison, T. F.; Jensen, K. F.; Monbaliu, J. M.; Myerson, A. S.; Revalor, E. M.; Senad, D. R.; Stelzer, T.; Weeranoppanant, N.; Wong, S.-Y.; Zhang, P. Scienc. 2016, 352, 61.
[4]
Liu, C.-G.; Xie, J.-X.; Wu, W.-B.; Wang, M.; Chen, W.-H.; Idres, S. B.; Rong, J.-W.; Deng, L.-W.; Khan, S. A.; Wu, J. Nat. Chem. 2021, 13, 451.
[5]
Liao, J.-Y.; Zhang, S.-L.; Wang, Z.-S.; Song, X.; Zhang, D.-L.; Kumar, R.; Jin, J.; Ren, P.; You, H.-Z.; Chen, F.-E. Green Synth. Catal. 2020, 1, 121.
[6]
Calabrese, G. S.; Pissavini, S. AIChE J. 2011, 57, 828.
[7]
Gutmann, B.; Cantillo, D.; Kappe, C. O. Angew. Chem. Int. Ed. 2015, 54, 6688.
[8]
Russell, M. G.; Jamison, T. F. Angew. Chem. Int. Ed. 2019, 58, 7678.
[9]
Gérardy, R.; Monbaliu, J.-C. M. Topics in Heterocyclic Chemistry, Vol. 56, Eds.: Sharma, U. K.; der Eycken, E. V., Springer Cham, 2018, p. 1.
[10]
Burcham, C. L.; Florence, A. J.; Johnson, M. D. Annu. Rev. Chem. Biomol. Eng. 2018, 9, 253.
[11]
Pastre, J. C.; Browne, D. L.; Ley, S. V. Chem. Soc. Rev. 2013, 42, 8849.
[12]
Cutler, R. A.; Stenger, R. J.; Suter, C. M. J. Am. Chem. Soc. 1952, 74, 5475.
[13]
(a) Horsberg, T. E.; Hoff, K. A.; Nordmo, R. J. Aquat. Anim. Healt. 1996, 8, 292.
[13]
(b) Shen, J.-Z.; Hu, D.-F.; Wu, X.-A.; Coats, J. R. J. Vet. Pharmacol. Ther. 2003, 26, 337.
[13]
(c) Ueda, Y.; Ohtsuki, S.; Narukawa, N. J. Vet. Med. Sci. 1995, 57, 261.
[13]
(d) Ehrlich, J.; Bartz, Q. R.; Smith, R. M.; Joslyn, D. A.; Burkholder, P. R. Scienc. 1947, 106, 417.
[13]
(e) Rebstock, M. C.; Crooks, H. M.; Controulis, J.; Bartz, Q. R. J. Am. Chem. Soc. 1949, 71, 2458.
[14]
Nitzan, O.; Supnitzky, U.; Kennes, Y.; Chazan, B.; Raul, R.; Colodner, R. Isr. Med. Assoc. J. 2010, 12, 371.
[15]
(a) Corey, E. J.; Choi, S. Tetrahedron Lett. 2000, 41, 2765.
[15]
(b) Hajra, S.; Karmakar, A.; Maji, T.; Medda, A. K. Tetrahedro. 2006, 62, 8959.
[15]
(c) Loncaric, C.; Wulff, W. D. Org. Lett. 2001, 3, 3675.
[16]
Xia, Y.-Q.; Jiang, M.-F.; Liu, M.-J.; Zhang, Y.; Qu, H.-M.; Xiong, T.; Huang, H.-S.; Cheng, D.; Chen, F.-E. J. Org. Chem. 2021, 86, 11557.
[17]
WHO Model List of Essential Medicines, 20th List, World Health Organization, 2017.
[18]
(a) Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Manninen, P. R.; Ulanowicz, D. A.; Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 673.
[18]
(b) Ramgren, S. D.; Silberstein, A. L.; Yang, Y.; Garg, N. K. Angew. Chem. Int. Ed. 2011, 50, 2171.
[18]
(c) Perrault, W. R.; Pearlman, B. A.; Godrej, D. B.; Jeganathan, A.; Yamagata, K.; Chen, J.-J.; Lu, C.-V.; Herrinton, P. M.; Gadwood, R. C.; Chan, L.; Lyster, M. A.; Maloney, M. T.; Moeslein, J. A.; Greene, M. L.; Barbachyn, M. R. Org. Process Res. Dev. 2003, 7, 533.
[19]
Russell, M. G.; Timothy, F. J. Angew. Chem. Int. Ed. 2019, 58, 7678.
[20]
Comer, E.; Organ, M. G. J. Am. Chem. Soc. 2005, 127, 8160.
[21]
(a) Concellón, J. M.; Suárez, J. R.; Solar, V. D. J. Org. Chem. 2005, 70, 7447.
[21]
(b) Brandt, J. C.; Elmore, S. C.; Wirth, R. I. Synlet. 2010, 20, 3099.
[21]
(c) Audiger, L.; Watts, K.; Elmore, S. C.; Wirth, R. I. ChemSusChe. 2012, 5, 257.
[21]
(d) Battilocchio, C.; Baxendale, I. R.; Biava, M.; Kitching, M. O.; Ley, S. V. Org. Process Res. Dev. 2012, 16, 798.
[22]
Magano J. Chem. Rev. 2009, 109, 4398.
[23]
Sagandira, C. R.; Paul, W. CN 113677658, 2021 [Chem. Abstr. 2021, 173, 581855]
[24]
WHO Report Standard Guidelines for the Clinical Management of Severe Influenza Virus Infections, World Health Organization , 2017.
[25]
Nie, L.-D.; Shi, X.-X. Tetrahedron: Asymmetry 2009, 20, 124.
[26]
Nie, L.-D.; Ding, W.; Shi, X.-X.; Quan, N.; Lu, X. Tetrahedron: Asymmetry 2012, 23, 742.
[27]
Nie, L.-D.; Shi, X.-X.; Ko, K. H.; Lu, W.-D. J. Org. Chem. 2009, 74, 3970.
[28]
Ogasawara, S.; Hayashi, Y. Synthesi. 2017, 49, 424.
[29]
Sagandira, C. R.; Paul, W. Synlet. 2020, 31, 1925.
[30]
Sriram, D.; Yogeeswari, P.; Srichakravarthy, N.; Bal, T. R. Bioorg. Med. Chem. Lett. 2004, 14, 1085.
[31]
Mateo, M. G.; Gutierrez, M. D. M.; Vidal, F.; Domingo, P. Expert Opin. Pharmacother. 2013, 14, 1055.
[32]
Horwitz, J. P.; Chua, J.; Noel, M.; Nucleosides, V. J. Org. Chem. 1964, 29, 2076.
[33]
Chen, B.-C.; Stark, D. R.; Baker, S. R.; Quinlan, S. L. EP 0653436, 1998.
[34]
Mansuri, M. M.; Starrett, J. E.; Wos, J. A.; Tortolani, D. R.; Brodfuehrer, P. R.; Howell, H. G.; Martin, J. C. J. Org. Chem. 1989, 54, 4780.
[35]
Discordia R. P. J. Labelled Compd. Radiopharm. 1996, 38, 613.
[36]
Chu, C.-K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z.-P.; Kosugi, Y.; Pullaiah, K. C.; Van, R. P. J. Org. Chem. 1989, 54, 2217.
[37]
Shiragami, H.; Irie, Y.; Shirae, H.; Yokozeki, K.; Yasuda, N. J. Org. Chem. 1988, 53, 5170.
[38]
Livni, E.; Berker, M.; Hillier, S.; Waller, S. C.; Ogan, M. D.; Discordia, R. P.; Rienhart, J. K.; Rubin, R. H.; Fischman, A. J. Nucl. Med. Biol. 2004, 31, 613.
[39]
Sagandira, C. R.; Akwi, F. M.; Sagandira, M. B.; Watts, P. J. Org. Chem. 2021, 86, 13934.
[40]
Chakkath, T.; Lavergne, S.; Fan, T. M.; Bunick, D.; Dirikolu, L. Vet. Sci. 2015, 2, 52.
[41]
Dirikolu, L.; Chakkath, T.; Fan, T.; Mente, N. R. J. Anal. Toxicol. 2009, 33, 595.
[42]
Kaina, B.; Christmann, M.; Naumann, S.; Roos, W. P. DNA Repai. 2007, 6, 1079.
[43]
Taylor, J. W.; Armstrong, T.; Kim, A. H.; Venere, M.; Acquaye, A.; Schrag, D.; Wen, P.-Y. Neuro Oncol. 2019, 21, 1.
[44]
Jaman, Z.; Sobreira, T. J. P.; Mufti, A.; Ferreira, C. R.; Cooks, R. G.; Thompson, D. H. Org. Process Res. Dev. 2019, 23, 334.
[45]
Zimmermann, J.; Buchdunger, E.; Mett, H.; Meyer, T.; Lydon, N. B.; Traxler, P. Bioorg. Med. Chem. Lett. 1996, 6, 1221.
[46]
Zimmermann, J.; Buchdunger, E.; Mett, H.; Meyer, T.; Lydon, N. B. Bioorg. Med. Chem. Lett. 1997, 7, 187.
[47]
Capdeville, R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Nat. Rev. Drug Discovery. 2002, 1, 493.
[48]
Deadman, B. J.; Hopkin, M. D.; Baxendale, I. R.; Ley, S. V. Org. Biomol. Chem. 2013, 11, 1766.
[49]
Hopkin, M. D.; Baxendale, I. R.; Ley, S.V. Chem. Commun. 2010, 46, 2450.
[50]
Fu, W.-C.; Jamison, T. F. Org. Lett. 2019, 21, 6112.
[51]
Antar, A. I.; Otrock, Z. K.; Jabbour, E.; Mohty, M.; Bazarbachi, A. Leukemi. 2020, 34, 682.
[52]
Naganna, N.; Opoku-Temeng, C.; Choi, E. Y.; Larocque, E.; Chang, E.-T.; Carter-Cooper, B. A.; Wang, M.; Torregrosa-Allen, S. E.; Elzey, B. D.; Lapidus, R. G.; Sintim, H. O. EBioMedicin. 2019, 40, 231.
[53]
Sperry, J. B.; Minteer, C. J.; Tao, J.-Y.; Johnson, R.; Duzguner, R.; Hawksworth, M.; Oke, S.; Richardson, P. F.; Barnhart, R.; Bill, D. R.; Giusto, R. A.; Weaver, J. D. Org. Process Res. Dev. 2018, 22, 1262.
[54]
Larocque, E. A.; Naganna, N.; Opoku-Temeng, C.; Lambrecht, A. M.; Sintim, H. O. Chem. Med. Chem. 2018, 13, 1172.
[55]
Biyani, S. A.; Qi, Q.-Q.; Wu, J.-Z.; Moriuchi, Y.; Larocque, E. A.; Sintim, H. O.; Thompson, D. H. Org. Process Res. Dev. 2020, 24, 2240.
[56]
Schuüller, J.; Cassidy, J.; Dumont, E.; Roos, B.; Durston, S.; Banken, L.; Utoh, M.; Mori, K.; Weidekamm, E.; Reigner, B. Cancer Chemother. Pharmacol. 2000, 45, 291.
[57]
Venturini M. Eur. J. Cance. 2002, 38, 3.
[58]
Koukourakis, G. V.; Kouloulias, V.; Koukourakis, M. J.; Zacharias, G. A.; Zabatis, H.; Kouvaris, J. Molecule. 2008, 13, 1897.
[59]
Shimma, N.; Umeda, I.; Arasakin, M.; Murasaki, C.; Masubuchi, K.; Kohchi, Y.; Miwa, M.; Ura, M. Bioorg. Med. Chem. 2000, 8, 1697.
[60]
Shen, B.; Jamison, T. F. Org. Lett. 2012, 14, 3348.
[61]
Miranda, L. S. D. M.; de Souza, R. O. M. A.; Lea?, R. A. C.; Carneiro, P. F.; Pedraza, S. F.; de Carvalho, O. V.; de Souza, S. P.; Neves, R. V. Org. Process Res. Dev. 2019, 23, 2516.
[62]
Heim, C.; Pliatsika, D.; Mousavizadeh, F.; B?r, K.; Alvarez, B. H.; Giannis, A.; Hartmann, M. D. J. Med. Chem. 2019, 62, 6615.
[63]
Ivanova, M.; Legros, J.; Poisson, T.; Jubault, P. J. Flow Chem. 2022, 12, 383.
[64]
Hoy S. M. Drug. 2016, 76, 509.
[65]
Wang, P.; Li, P.-X.; Gu, X.-Y. WO 2015054960, 2015 [Chem. Abstr. 162, 564086]
[66]
Meng, Q.; Zhao, T.; Kang, D.-W.; Huang, B.-S.; Zhan, P.; Liu, X.-Y. Chem. Cent. J. 2017, 11, 1.
[67]
Halama, A.; Stach, J.; Rádl, S.; Benediktová, K. Org. Process Res. Dev. 2018, 22, 1861.
[68]
Huang, Y.; Xu, H.; Zhang, Y.-B.; Zheng, F. CN 105399694, 2016 [Chem. Abstr. 2016, 164, 438099]
[69]
Wang, J.-F.; Zeng, W.-Q.; Li, S.-H.; Shen, L.; Gu, Z.-X.; Zhang, Y.; Li, J.; Chen, S.-H.; Jia, X.-B. ACS Med. Chem. Lett. 2017, 8, 299.
[70]
Chen, W.-Q.; Luo, J.; Liu, L.-X.; Fan, Y.-P. WO 2014198241, 2014 [Chem. Abstr. 2014, 162, 82161]
[71]
Gunic, E.; Girardet, J. L.; Vernier, J. M.; Tedder, M. E.; Paisner, D. A. US 8173690, 2010 [Chem. Abstr. 2010, 152, 311613]
[72]
Dami?o, M. C. F. C. B.; Mar?on, H. M.; Pastre, J. C. React. Chem. Eng. 2020, 5, 865.
[73]
Grafe, I.; Schickaneder, H.; Ahrens, K. H. US 4978773, 1990 [Chem. Abstr. 1990, 113, 190940]
[74]
(a) Chen, F.; Deng, Y.; Wan, J. Chin. J. Pharm. 1998, 29, 339.
[74]
(b) Wadia, M. S.; Patil, D. V. Synth. Commun. 2003, 33, 2725.
[75]
Maiorana, S.; Galliani, G.; Chiodini, G.; WO 1992022522, 1992.
[76]
Wang, L.-L.; Liu, M.-J.; Jing, M.-F.; Wan, L.; Li, W.-J.; Cheng, D.; Chen, F.-E. Chem. Eur. J. 2022, 28, 1.
[77]
Bédard, A. C.; Adamo, A.; Aroh, K. C.; Russell, M. G.; Bedermann, A. A.; Torosian, J.; Yue, B.; Jensen, K. F.; Jamison, T. F. Scienc. 2018, 361, 1220.
[78]
Adamo, A.; Beingessner, R. L.; Behnam, M.; Chen, J.; Jamison, T. F.; Jensen, K. F.; Monbaliu, J. C. M.; Myerson, A. S.; Revalor, E. M.; Snead, D. R.; Stelzer, T.; Weeranoppanant, N.; Wong, S.-Y.; Zhang, P. Scienc. 2016, 352, 61.
[79]
Kumar, S. V.; Singh, A. K.; Pabbaraja, S. Org. Process Res. Dev. 2019. 23, 1892.
[80]
(a) Kolodych, S.; Rasolofonjatovo, E.; Chaumontet, M.; Nevers, M.-C.; Créminon, C.; Taran, F. Angew. Chem. Int. Ed. 2013, 52, 12056.
[80]
(b) Browne, D. L.; Taylor, J. B.; Plant, A.; Harrity, J. P. A. J. Org. Chem. 2010, 75, 984.
[80]
(c) Decuypere, E.; Specklin, S.; Gabillet, S.; Audisio, D.; Liu, H.; Plougastel, L.; Kolodych, S.; Taran, F. Org. Lett. 2015, 17, 362.
[81]
Comas-Barceló, J.; Blanco-Ania, D.; van den Broek, S. A. M. W.; Nieuwland, P. J.; Harrity, J. P. A.; Rutjes, F. P. J. T. Catal. Sci. Technol. 2016, 6, 4718.
[82]
Poh, J.-S.; Browne, D. L.; Ley, S. V. React. Chem. Eng. 2016, 1, 101.
[83]
Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. V. J. Comb. Chem. 2004, 6, 332.
[84]
(a) Firth, B. E.; Rosen, R. J. US 4447657, 1984 [Chem. Abstr. 1984, 101, 72420]
[84]
(b) Firth B. E. US 4275248, 1981 [Chem. Abstr. 1981, 95, 115041]
[84]
(c) Ecke, G. G.; Kolka, A. J. US 2831898, 1958 [Chem. Abstr. 1958, 52, 92696]
[84]
(d) Napolitano J. P. US 3367981, 1968 [Chem. Abstr. 1968, 69, 51823]
[84]
(e) Buls, V. W.; Miller, R. S. US 2923745, 1960 [Chem. Abstr. 1960, 54, 50254]
[85]
(a) Stroh, R.; Seydel, R.; Hahn, W. Ang. Chem. 1957, 69, 699.
[85]
(b) Kolka, A. J.; Napolitano, J. P.; Filbey, A. H.; Ecke, G. G. J. Org. Chem. 1957, 22, 642.
[86]
(a) Davuluri, R.; Ponnalah, R.; Kumar, N.; Nimmakayala, N.; Reddy, M. WO 2013035103, 2013 [Chem. Abstr. 2013, 158, 418524]
[86]
(b) Sharma, A. K.; Pandey, M.; Giri, A.; Sokhi, S. S.; Singh, G.; Lahiri, S.; Cabri, W. WO 2021191832, 2021 [Chem. Abstr. 2021, 176, 305237]
[87]
Pramanik, C.; Kotharkar, S.; Patil, P.; Gotrane, D.; More, Y.; Borhade, A.; Chaugule, B.; Khaladkar, T.; Neelakandan, K.; Chaudhari, A.; Kulkarni, M. G.; Tripathy, N. K.; Gurjar, M. K. Org. Process Res. Dev. 2014, 18, 152.
[88]
Mougeot, R.; Jubault, P.; Legros, J.; Poisson, T. Molecule. 2021, 26, 7183.
[89]
Martins, G. M.; Magalh?es, M. F. A.; Brocksom, T. J.; Bagnato, V. S.; de Oliveira, K. T. J. Flow Chem. 2022, 12, 371.
[90]
Vinet, L.; Marco, L. D.; Kairouz, V.; Charette, A. B. Org. Process Res. Dev. 2022, 26, 2330.
[91]
Kadhum, W. R.; Hijikuro, T. O.; Kenji, I. T.; Mark, S. Eur. J. Pharm. Sci. 2016, 88, 282.
[92]
Gutmann, B.; Cantillo, D.; Kappe, C. O. Angew. Chem. Int. Ed. 2015, 54, 6688.
[93]
Fran?a, A. d. S.; Le?o, R. A. C.; de Souza, R. O. M. A. J. Flow Chem. 2020, 10, 563.
[94]
(a) Liu, H.; Zhen, X.-C.; Sun, H.-F.; Zhu, L.-Y.; Qian, W.-K.; Yu, L.-P.; Li, Z.; Cai, W.-X.; Jiang, H.-L.; Chen, K.-X. CN 102796096, 2012 [Chem. Abstr. 2012, 160, 473334]
[94]
(b) Zhang, Z.-H.; Zhang, H.-J.; Deng, A.-J.; Wang, B.; Li, Z.-H.; Liu, Y.; Wu, L.-Q.; Wang, W.-J.; Qin, H.-L. J. Med. Chem. 2015, 58, 7557.
[94]
(c) Li, Y.-H.; Yang, P.; Kong, W.-J.; Wang, Y.-X.; Hu, C.-Q.; Zuo, Z.-Y.; Wang, Y.-M.; Gao, H.; Gao, L.-M.; Feng, Y.-C.; Du, N.-N.; Liu, Y.; Song, D.-Q.; Jiang, J.-D. J. Med. Chem. 2009, 52, 492.
[94]
(d) Wu, S.; Wang, D.-M.; Wei, J.-Z. CN 103421003, 2012 [Chem. Abstr. 2012, 160, 34019]
[95]
(a) Yu, J.-X.; Zhang, Z.-H.; Zhou, S.-Q.; Zhang, W.; Tong, R.-B. Org. Chem. Front. 2018, 5, 242.
[95]
(b) Sun, H.-F.; Zhu, L.-Y.; Yang, H.-C.; Qian, W.-K.; Guo, L.; Zhou, S.-B.; Gao, B.; Li, Z.; Zhou, Y.; Jiang, H.-L.; Chen, K.-X.; Zhen, X.-C. Bioorg. Med. Chem. 2013, 21, 856.
[96]
Li, W.-J.; Jing, M.-F.; Liu, M.-J.; Lin, X.; Xia, Y.-Q.; Wan, L.; Chen, F.-E. Chem. Eur. J. 2022, 28, 1.
[97]
Sigel, E.; Ernst, M. Trends Pharmacol. Sci. 2018, 39, 659.
[98]
McDonough, J. A.; Durrwachter, J. R. Org. Process Res. Dev. 1997, 1, 268.
[99]
Liu, G.; Wang, H.-B.; Liu, X.-S. CN 112898203, 2021 [Chem. Abstr. 2021, 175, 209188]
[100]
Alharthy R. D. Pharm. Chem. J. 2020, 54, 273.
[101]
Prajuli, R.; Banerjee, J.; Khanal, H. Orient. J. Chem. 2015, 31, 2099.
[102]
Shrivastava, P.; Singh, P.; Tewari, A. K. Med. Chem. Res. 2012, 21, 2465.
[103]
Tewari, A. K.; Singh, V. P.; Yadav, P.; Gupta, G.; Singh, A.; Goel, R. K.; Shinde, P.; Mohan, C. G. Bioorg. Chem. 2014, 56, 8.
[104]
Beyrati, M.; Hasaninejad, A. Org. Prep. Proced. Int. 2016, 5, 393.
[105]
Sun, P.-F.; Yang, D.-S.; Wei, W.; Sun, X.-J.; Zhang, W.-H.; Zhang, H.; Wang, Y.; Wang, H. Tetrahedro. 2017, 73, 2022.
[106]
Zakerinasab, B.; Nasseri, M. A.; Hassani, H.; Samieadel, M. M. Res. Chem. Intermedia. 2016, 42, 3169.
[107]
Zhou, S.-H.; Hong, Q.-S.; Mei, W.-L.; He, Y.; Wu, C.-J.; Sun, T.-M. Org. Process Res. Dev. 2021, 25, 2146.
[108]
Plutschack, M. B.; Pieber, B.; Gilmore, K.; Seeberger, P. H. Chem. Rev. 2017, 117, 11796.
[109]
Liu, D.; Zhu, Y.-Y.; Gu, S.-X.; Chen, F.-E. Chin. J. Org. Chem. 2021, 41, 1002 (in Chinese).
[109]
(刘玎, 朱园园, 古双喜, 陈芬儿, 有机化学. 2021, 41, 1002.)
[110]
Li, J.-P.; Huang, S.-T.; Yang, Q.; Li, W.-Q.; Liu, T.; Huang, C. Chin. J. Org. Chem. 2023, 43, 1550 (in Chinese).
[110]
(李靖鹏, 黄顺桃, 杨棋, 李伟强, 刘腾, 黄超, 有机化学. 2023, 43, 1550.)
[111]
Cheng, D.; Chen, F.-E. Chem. Ind. Eng. Prog. 2019, 38, 556 (in Chinese).
[111]
(程荡, 陈芬儿, 化工进展. 2019, 38, 556.)
Outlines

/