Recent Advances in the Synthesis of 5-(Hetero)aryl Uracil Derivatives

Zhao-Li Wang; An-Di Liu; Li Liu; Liang Cheng

doi:10.1055/a-2091-1071

Synlett, Table of Contents

Synlett 2024; 35(06): 603-615
DOI: 10.1055/a-2091-1071

account

Special Issue to Celebrate the Centenary Year of Prof. Har Gobind Khorana

Recent Advances in the Synthesis of 5-(Hetero)aryl Uracil Derivatives

Zhao-Li Wang

^aBeijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China

^bHangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, P. R. of China

,

An-Di Liu

^aBeijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China

^cUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Li Liu

^aBeijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China

^cUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Liang Cheng ∗

^aBeijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China

^bHangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, P. R. of China

^cUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Dedicated to Professor Yong-Jun Chen on the occasion of his 60^th birthday.

Abstract

C5-Aryl/heteroaryl uracil-based compounds have attracted continuous interest because of their wide biological potential. In this review, we outline the primary synthetic methods used to prepare designated uracils, various combinations of which have been used to synthesize target compounds with potential biological activities. The significance of each approach and its limitations are also summarized.

1 Introduction

2 Coupling of Prefunctionalized Uracils with (Hetero)aryl Reagents

2.1 Negishi Coupling

2.2 Suzuki–Miyaura Coupling

2.3 Stille Coupling

3 Coupling of Functionalized Uracils with Nonactivated Aromatic (Hetero)cycles

3.1 Photochemically Induced Coupling

3.2 Palladium-Catalyzed Coupling

4 Coupling of Nonactivated Uracil/Uridine with Functionalized Aromatic (Hetero)cycles

4.1 Electrochemical Reduction

4.2 Transition-Metal-Catalyzed Coupling

4.3 Light-Promoted Coupling of Uracils with Diazonium Salts

5 Direct Coupling of Nonactivated Uracils with Nonactivated Aromatic (Hetero)cycles

6 Summary and Prospects

Key words

uracils - cross-coupling reaction - prefunctionalization - direct coupling - nucleosides - medicinal chemistry

Full Text

References

References
1 Lagoja IM. Chem. Biodiversity 2005; 2: 1
2 Ascoli A. Hoppe-Seyler’s Z. Physiol. Chem. 1901; 31: 161
3 Brown DJ. The Pyrimidines: The Chemistry of Heterocyclic Compounds, Vol. 52. Wiley; New York: 1994
4 Heidelberger C, Chaudhuri NK, Danneberg P, Mooren D, Griesbach L, Duschinsky R, Schnitzer RJ, Pleven E, Scheiner J. Nature 1957; 179: 663
5 Novikov MS, Geisman AN. Chem. Heterocycl. Compd. (N. Y.) 2014; 49: 1426
6 Pałasz A, Cież D. Eur. J. Med. Chem. 2015; 97: 582
7 Grabovskiy SA, Murinov YI, Kabal’nova NN. Curr. Org. Chem. 2012; 16: 2389
8 Xin-Ying Z, Yang-Yang W, Dong F, Xue-Sen FA. N. Youji Huaxue 2010; 30: 797
9 Baker BR, Kawazu M. J. Med. Chem. 1967; 10: 311
10 Bedi RK, Huang D, Wiedmer L, Li Y, Dolbois A, Wojdyla JA, Sharpe ME, Caflisch A, Sledz P. ACS Chem. Biol. 2020; 15: 618
11 Lamb YN. Drugs 2018; 78: 1501
12 Wen Z, Suzol SH, Peng J, Liang Y, Snoeck R, Andrei G, Liekens S, Wnuk SF. Arch. Pharm. (Weinheim, Ger.) 2017; 350: 1700023
13 Peyron C, Benhida R, Bories C, Loiseau PM. Bioorg. Chem. 2005; 33: 439
14 Pesnot T, Tedaldi LM, Jambrina PG, Rosta E, Wagner GK. Org. Biomol. Chem. 2013; 11: 6357
15 Bardagí JI, Rossi RA. Org. Prep. Proced. Int. 2009; 41: 479
16 Wagner GK, Pesnot T, Palcic MM, Jørgensen R. J. Biol. Chem. 2015; 290: 31162
17 Meltzer D, Ethan O, Arguin G, Nadel Y, Danino O, Lecka J, Sévigny J, Gendron F.-P, Fischer B. Bioorg. Med. Chem. 2015; 23: 5764
18 Dalager M, Andersen NK, Kumar P, Nielsen P, Sharma PK. Org. Biomol. Chem. 2015; 13: 7040
19 Kovaliov M, Wachtel C, Yavin E, Fischer B. Org. Biomol. Chem. 2014; 12: 7844
20 Fritz Y, Wagenknecht H.-A. Front. Chem. 2019; 7: 659
21 Pawar MG, Nuthanakanti A, Srivatsan SG. Bioconjugate Chem. 2013; 24: 1367
22 Tanpure AA, Srivatsan SG. Chem. Eur. J. 2011; 17: 12820
23 Greco NJ, Tor Y. Tetrahedron 2007; 63: 3515
24 Greco NJ, Tor Y. J. Am. Chem. Soc. 2005; 127: 10784
25 Sidduri A, Tilley JW, Lou J, Tare N, Cavallo G, Frank K, Pamidimukkala A, Choi DS, Gerber L, Railkar A, Renzetti L. Bioorg. Med. Chem. Lett. 2013; 23: 1026
26 Das K, Pink M, Rajca S, Rajca A. J. Am. Chem. Soc. 2006; 128: 5334
27 Majid TN, Knochel P. Tetrahedron Lett. 1990; 31: 4413
28 Duddu R, Eckhardt M, Furlong M, Knoess HP, Berger S, Knochel P. Tetrahedron 1994; 50: 2415
29 Stevenson TM, Prasad AS. B, Citineni JR, Knochel P. Tetrahedron Lett. 1996; 37: 8375
30 Bhanu Prasad AS, Stevenson TM, Citineni JR, Nyzam V, Knochel P. Tetrahedron 1997; 53: 7237
31 Gong L.-Z, Knochel P. Synlett 2005; 267
32 Balkenhohl M, Ziegler DS, Desaintjean A, Bole LJ, Kennedy AR, Hevia E, Knochel P. Angew. Chem. Int. Ed. 2019; 58: 12898
33 Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
34 Miyaura N, Suzuki A. J. Chem. Soc., Chem. Commun. 1979; 866
35 Gallagher-Duval S, Hervé G, Sartori G, Enderlin G, Len C. New J. Chem. 2013; 37: 1989
36 Rahman M, Ghosh S, Bhattacherjee D, Zyryanov GV, Bagdi Kumar A, Hajra A. Asian J. Org. Chem. 2022; 11: e202200179
37 Lussier T, Hervé G, Enderlin G, Len C. RSC Adv. 2014; 4: 46218
38 Serrano JL. Chem. Rec. 2022; 22: e202200179
39 Shih Y.-C, Chien T.-C. Tetrahedron 2011; 67: 3915
40 Čapek P, Cahová H, Pohl R, Hocek M, Gloeckner C, Marx A. Chem. Eur. J. 2007; 13: 6196
41 Cahová H, Havran L, Brázdilová P, Pivoñková H, Pohl R, Fojta M, Hocek M. Angew. Chem., Int. Ed. Engl. 2008; 47: 2059
42 Raindlová V, Pohl R, Šanda M, Hocek M. Angew. Chem. Int. Ed. 2010; 49: 1064
43 Sartori G, Enderlin G, Hervé G, Len C. Synthesis 2012; 44: 767
44 Sartori G, Hervé G, Enderlin G, Len C. Synthesis 2013; 45: 330
45 Ejlersen M, Lou C, Sanghvi YS, Tor Y, Wengel J. Chem. Commun. 2018; 54: 8003
46 Fresneau N, Hiebel M.-A, Agrofoglio LA, Berteina-Raboin S. Molecules 2012; 17: 14409
47 Kapdi A, Gayakhe V, Sanghvi YS, García J, Lozano P, da Silva I, Pérez J, Serrano JL. RSC Adv. 2014; 4: 17567
48 Gayakhe V, Ardhapure A, Kapdi AR, Sanghvi YS, Serrano JL, García L, Pérez J, García J, Sánchez G, Fischer C, Schulzke C. J. Org. Chem. 2016; 81: 2713
49 Bhilare S, Gayakhe V, Ardhapure AV, Sanghvi YS, Schulzke C, Borozdina Y, Kapdi AR. RSC Adv. 2016; 6: 83820
50 Serrano JL, Gaware S, Pérez JA, Pérez J, Lozano P, Kori S, Dandela R, Sanghvi YS, Kapdi AR. Dalton Trans. 2022; 51: 2370
51 Shaughnessy KH. Chem. Rec. 2022; 22: e202200190
52 Handa S, Andersson MP, Gallou F, Reilly J, Lipshutz BH. Angew. Chem. Int. Ed. 2016; 55: 4914
53 Serrano JL, García L, Pérez J, Lozano P, Correia J, Kori S, Kapdi AR, Sanghvi YS. Organometallics 2020; 39: 4479
54 Soli ED, Surber BW, Reed AD. J. Labelled Compd. Radiopharm. 2021; 64: 254
55 Hirano K, Miura M, Miura W. Synthesis 2017; 49: 4745
56 Snieckus V, Quesnelle C. Synthesis 2018; 50: 4413
57 Dow NW, Pedersen PS, Chen TQ, Blakemore DC, Dechert-Schmitt A.-M, Knauber T, MacMillan DW. C. J. Am. Chem. Soc. 2022; 144: 6163
58 Wicke L, Engels JW. Bioconjugate Chem. 2012; 23: 627
59 Zhang X.-H, Xu Y.-Z. Magn. Reson. Chem. 2016; 54: 887
60 Krause A, Hertl A, Muttach F, Jäschke A. Chem. Eur. J. 2014; 20: 16613
61 Seki K.-i, Matsuda K, Ohkura K. Chem. Lett. 1987; 16: 175
62 Ohkura K, Sugaoi T, Nishijima K.-I, Kuge Y, Seki K.-i. Tetrahedron Lett. 2002; 43: 3113
63 Yang Q, Wei T, He Y, Liang Y, Zhang Z.-T. Helv. Chim. Acta 2015; 98: 953
64 Saporito D, Rodriguez SA, Baumgartner MT. Aust. Chem. J. 2019; 72: 978
65 Rossi RA, Pierini AB, Peñéñory AB. Chem. Rev. 2003; 103: 71
66 Franchi L, Rinaldi M, Vignaroli G, Innitzer A, Radi M, Botta M. Synthesis 2010; 3927
67 Liang Y, Gloudeman J, Wnuk SF. J. Org. Chem. 2014; 79: 4094
68 Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
69 Arun V, Reddy PO. V, Pilania M, Kumar D. Eur. J. Org. Chem. 2016; 2096
70 Médebielle M, Oturan MA, Pinson J, Savéant J.-M. Tetrahedron Lett. 1993; 34: 3409
71 Balasubramaniyam T, Oh K.-I, Jin H.-S, Ahn H.-B, Kim B.-S, Lee J.-H. Int. J. Mol. Sci. 2021; 22: 9552
72 Čerñová M, Pohl R, Hocek M. Eur. J. Org. Chem. 2009; 3698
73 Čerñová M, Čerña I, Pohl R, Hocek M. J. Org. Chem. 2011; 76: 5309
74 Shang Y, Wu C, Gao Q, Liu C, Li L, Zhang X, Cheng H.-G, Liu S, Zhou Q. Nat. Commun. 2021; 12: 2988
75 Ball LT, Lloyd-Jones GC, Russell CA. Science 2012; 337: 1644
76 Cresswell AJ, Lloyd-Jones GC. Chem. Eur. J. 2016; 22: 12641
77 Liu A.-D, Wang Z.-L, Liu L, Cheng L. J. Org. Chem. 2021; 86: 16434
78 Liu A.-D, Wang Z.-L, Liu L, Cheng L. Curr. Protoc. 2022; 2: e432
79 Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
80 Kim KH, Lee HS, Kim JN. Tetrahedron Lett. 2011; 52: 6228
81 Chen F, Feng Z, He C.-Y, Wang H.-Y, Guo Y.-L, Zhang X. Org. Lett. 2012; 14: 1176
82 Kianmehr E, Torabi M, Khalkhali Rezazadeh M, Faghih N, Khan KM. Eur. J. Org. Chem. 2015; 2796
83 Davarani SS. H, Fumani NS, Arvin-Nezhad H, Moradi F. Tetrahedron Lett. 2008; 49: 710
84 Das VK, Bharali P, Konwar BK, Mikkola J.-P, Shchukarev A, Thakur AJ. New J. Chem. 2016; 40: 1935