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Synthesis 2021; 53(08): 1524-1530
DOI: 10.1055/s-0040-1706103
DOI: 10.1055/s-0040-1706103
paper
Organophotoredox-Catalyzed C–H Alkylation of Imidazoheterocycles with Malonates: Total Synthesis of Zolpidem
Dr. Narendra R. Chaubey acknowledges the Research Fellowship (F. No. 45/15/2019-BIO/BMS) from Indian Council of Medical Research, Delhi, India.
Abstract
Organophotocatalytic C–H bond functionalization has attracted a lot of attention in the past several years due to the possibility of catalyzing reactions in a metal- and peroxide-free environment. Continuing on these lines, an organophotoredox-catalyzed C–H functionalization of imidazo[1,2-a]pyridines and related heterocycles with bromomalonates under mild conditions is reported, providing excellent yields of the products at room temperature. This is the first report involving malonates as coupling partners leading to the synthesis of a range of functionalized products including total synthesis of zolpidem, a sedative-hypnotic drug molecule.
Key words
organophotoredox - C–H functionalization - imidazoheterocycles - zolpidem - drug prejudiceSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706606.
- Supporting Information
Publication History
Received: 28 October 2020
Accepted after revision: 29 October 2020
Article published online:
02 December 2020
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References
- 1 Almirante L, Polo L, Mugnaini A, Provinciali E, Biancotti A, Gamba A, Murmann W. J. Med. Chem. 1965; 8: 305
- 2a Puerstinger G, Paeshuyse J, De Clercq E, Neyts J. Bioorg. Med. Chem. Lett. 2007; 17: 390
-
2b
Townsend LB.
Patent WO 9727205A1, 1997
- 2c Elhakmaoui A, Gueiffier A, Milhavet J.-C, Blache Y, Chapat J.-P, Chavignon O, Teulade J.-C, Snoeck R, Andrei G, De Clercq E. Bioorg. Med. Chem. Lett. 1994; 4: 1937
- 2d Gudmundsson KS, Williams JD, Drach JC, Townsend LB. J. Med. Chem. 2003; 46: 1449
- 3a Byth KF, Culshaw JD, Green S, Oakes SE, Thomas AP. Bioorg. Med. Chem. Lett. 2004; 14: 2245
- 3b Revankar GR, Matthews TR, Robins RK. J. Med. Chem. 1975; 18: 1253
- 3c Fisher MH, Lusi A. J. Med. Chem. 1972; 15: 982
- 3d Cheng Y, Moraski GC, Cramer J, Miller MJ, Schorey JS. PLoS One 2014; 9: e87483
- 4a Piantanida MI, Kralj M, Suman L, Pavelicand K, Karminski-Zamola G. J. Med. Chem. 2008; 51: 4899
- 4b Hranjec M, Kralj M, Piantanida MI, Sedic M, Suman L, Pavelic K, Karminski-Zamola G. J. Med. Chem. 2007; 50: 5696
- 4c Badawey E, Kappe T. Eur. J. Med. Chem. 1995; 30: 327
- 5 Kaminski JJ, Bristol JA, Puchalski C, Lovey RG, Elliott AJ, Guzik H, Solomon DM, Conn DJ, Domalski MS. J. Med. Chem. 1985; 28: 876
- 6a Lacerda RB, de Lima CK. F, Da Silva LL, Romeiro NC, Miranda AL. P, Barreiro EJ, Fraga CA. M. Bioorg. Med. Chem. 2009; 17: 74
- 6b de Blas CJ, Del Prado M, Gruber J, Heinz BA, Vance L. J. Med. Chem. 1999; 42: 50
- 7 Stasyuk AJ, Banasiewicz M, Cyranski MK, Gryko DT. J. Org. Chem. 2012; 77: 5552
- 8 Tashrifi Z, Mohammadi-Khanaposhtani M, Larijani B, Mahadavi M. Eur. J. Org. Chem. 2020; 269
- 9a Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
- 9b Shi L, Xia W. Chem. Soc. Rev. 2012; 41: 7687
- 9c Chen JR, Hu XQ, Lu LQ, Xiao WJ. Acc. Chem. Res. 2016; 49: 1911
- 9d Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
- 9e Furst L, Matsuura BS, Narayanam JM. R, Tucker JW, Stephenson CR. J. Org. Lett. 2010; 12: 3104
- 10 Ravelli D, Fagnoni M, Albini A. Chem. Soc. Rev. 2013; 42: 97
- 11 Kibriya G, Bagdi AK, Hajra A. J. Org. Chem. 2018; 83: 10619
- 12 Mendoza PL, Diaz JE, Loaiza AE, Miranda LD. Tetrahedron 2018; 74: 5494
- 13 Qu C.-H, Song G.-T, Xu J, Yan W, Zhou C.-H, Li HY, Chen Z.-Z, Xu Z.-G. Org. Lett. 2019; 21: 8169
- 14 Sun P, Yang D, Wei W, Jiang M, Wang Z, Zhang L, Zhang H, Zhang Z, Wang Y, Wang H. Green Chem. 2017; 19: 4785
- 15 Rahman R, Das S, Barman P. Green Chem. 2018; 20: 141
- 16 Singsardar M, Mondal S, Laru S, Hajra A. Org. Lett. 2019; 21: 5606
- 17 Chen H, Yi H, Tang Z, Bian C, Zhang H, Lei A. Adv. Synth. Catal. 2018; 360: 3220
- 18 Zhu Z.-Q, Xiao L.-J, Zhou C.-C, Song H.-L, Xie Z.-B, Le Z.-G. Tetrahedron Lett. 2018; 59: 3326
- 19 Chang Q, Liu Z, Yu PL, Sun P. J. Org. Chem. 2017; 82: 5391
- 20 Samanta S, Ravi C, Rao SN, Joshi A, Adimurthy S. Org. Biomol. Chem. 2017; 15: 9590
- 21 Yin G, Zhu M, Fu W. Heterocycl. Commun. 2017; 23: 275
- 22 Liang D, Li L, Lynch C, Mackowiak B, Hedrich WD, Ai Y, Yin Y, Heyward S, Xia M, Wang H, Xue F. Eur. J. Med. Chem. 2019; 179: 84
- 23 Nair DK, Mobin SM, Namboothiri IN. N. Org. Lett. 2012; 14: 4580
- 24 Usami K, Nagasawa Y, Yamaguchi E, Tada N, Itoh A. Org. Lett. 2016; 18: 8
- 25 Chaubey NR, Kapdi AR, Maity B. ChemRxiv 2020; preprint
- 26 Huang H, Dang P, Wu L, Liang Y, Liu J. Tetrahedron Lett. 2016; 57: 574