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Synthesis 2020; 52(23): 3622-3631
DOI: 10.1055/s-0040-1707228
DOI: 10.1055/s-0040-1707228
paper
A PASE Approach to the Synthesis of Benzimidazopurines as Polycondensed Purine Derivatives
The reported study was funded by Russian Foundation for Basic Research (RFBR), project number 19-33-90161.Further Information
Publication History
Received: 16 June 2020
Accepted after revision: 01 July 2020
Publication Date:
06 August 2020 (online)
Abstract
A highly efficient PASE approach to a new class of polycyclic purine derivatives has been proposed. The strategy includes a consecutive reduction, auto-aromatization, and heterocyclization of the initial nitrobenzimidazopyrimidines obtained by a three-component condensation. It was shown that reduction of nitrobenzimidazopyrimidines by metals in acidic media was more efficient than heterogeneous hydrogenation. Novel derivatives of benz[4,5]imidazo[1,2-a]purines were obtained in good yields and the proposed structure was confirmed by X-ray crystal structure analysis. The obtained convergent benzimidazopurines combine two relevant medicinal chemistry scaffolds – benzimidazole and purine.
Key words
nitrogen heterocycles - nitrobenzimidazopyrimidines - polycycles - benzimidazopurines - reductive autoaromatizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707228.
- Supporting Information
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References
- 1 Bräse S. Privileged Scaffolds in Medicinal Chemistry. Design, Synthesis, Evaluation. RSC; Cambridge: 2015
- 2 Rusinov VL, Charushin VN, Chupakhin ON. Russ. Chem. Bull. 2018; 67: 573
- 3 Oukoloff K, Lucero B, Francisco KR, Brunden KR, Ballatore C. Eur. J. Med. Chem. 2019; 165: 332
- 4 Zhang N, Ayral-Kaloustian S, Nguyen T, Afragola J, Hernandez R, Lucas J, Gibbons J, Beyer C. J. Med. Chem. 2007; 50: 319
- 5 Savateev K, Fedotov V, Butorin I, Eltsov O, Slepukhin P, Ulomsky E, Rusinov V, Litvinov R, Babkov D, Khokhlacheva E, Radaev P, Vassiliev P, Spasov A. Eur. J. Med. Chem. 2020; 185: 111808
- 6a Kouadri Y, Ouahrani MR, Missaoui BE, Chebrouk F, Gherraf N. Asian J. Chem. 2015; 27: 3675
- 6b Farghaly TA, Abdallah MA, Aziz MR. A. Molecules 2012; 17: 14625
- 7 Bharate SB, Mahajan TR, Gole YR, Nambiar M, Matan TT, Kulkarni-Almeida A, Balachandran S, Junjappa H, Balakrishnan A, Vishwakarma RA. Bioorg. Med. Chem. 2008; 16: 7167
- 8a Reddy MV, Reddy GC. S, Jeong YT. RSC Adv. 2015; 5: 11423
- 8b Neo-choritis CG, Zarganes-Tzitzikas T, Tsoleridis CA, Stephanidou-Stephanatou J, Kontogiorgis CA, Hadjipavlou-Litina DJ, Choli-Papadopoulou T. Eur. J. Med. Chem. 2011; 46: 297
- 9 Abdel-Hafez AA.-M. Arch. Pharm. Res. 2007; 30: 678
- 10 Zanatta N, Amaral SS, Esteves-Souza A, Echevarria A, Brondani PB, Flores DC, Bonacorso HG, Flores AF. C, Martins MA. P. Synthesis 2006; 2305
- 11 Ishida J, Wang H.-K, Oyama M, Cosentino ML, Hu C.-Q, Lee K.-H. J. Nat. Prod. 2001; 64: 958
- 12 Poojali PW, Priyanka TP, Kirti TP, Dattatraya KJ, Govind BK, Prashant VA. Synth. Commun. 2016; 46: 2022
- 13 Savateev KV, Ulomsky EN, Fedotov VV, Rusinov VL, Sivak KV, Lyubishin MM, Kuzmich NN, Aleksandrov AG. Bioorg. Khim. 2017; 43: 421
- 14 Spasov AA, Babkov DA, Sysoeva VA, Litvinov RA, Shamshina DD, Ulomsky EN, Savateev KV, Fedotov VV, Slepukhin PA, Chupakhin ON, Charushin VN, Rusinov VL. Arch. Pharm. (Weinheim) 2017; 350: e1700226
- 15 Chupakhin ON, Charushin VN, Rusinov VL, Ulomskii EN, Kotovskaya SK, Kiselev OI, Deeva EG, Savateev KV, Borisov SS. RU Patent 2529487, 2014
- 16 Savateev KV, Ulomsky EN, Borisov SS, Voinkov EK, Fedotov VV, Rusinov VL. Chem. Heterocycl. Compd. 2014; 50: 880
- 17a Zhao L, Christov P, Kozekov ID, Pence MG, Pallan PS, Rizzo CJ, Egli M, Guengerich FP. Angew. Chem. Int. Ed. 2012; 51: 5466
- 17b Combs D, Langevine CM, Qiu Y, Zusi FC. Patent WO 2005/011609, 2004
- 18a Jadhav AM, Kim YI, Lim KT, Jeong YT. Tetrahedron Lett. 2018; 59: 554
- 18b Reddy MV, Byeon KR, Park SH, Kim DW. Tetrahedron 2017; 73: 5289
- 18c Fedotov VV, Ulomskiy EN, Gorbunov EB, Eltsov OS, Voinkov EK, Savateev KV, Drokin RA, Kotovskaya SK, Rusinov VL. Chem. Heterocycl. Compd. 2017; 53: 582
- 19 Biron KK, Harvey RJ, Chamberlain SC, Good SS, Smith AA. III, Davis MG, Talarico CL, Miller WH, Ferris R, Dornsife RE, Stanat SC, Drach JC, Townsend LB, Koszalka GW. Antimicrob. Agents Chemother. 2002; 46: 2365
- 20 El-Gendy MM. A, Shaaban M, Shaaban KA, El-Bondkly AM, Laatsch H. J. Antibiot. 2008; 61: 149
- 21 Hazra S, Konrad M, Lavie AJ. Med. Chem. 2010; 53: 5792
- 22 Zhang W., Yi W.-B.; Pot, Atom, and Step Economy (PASE) Synthesis, SpringerBriefs in Green Chemistry for Sustainability; https://doi.org/10.1007/978-3-030-22596
- 23 Rao HS. P, Geetha K. Tetrahedron Lett. 2009; 50: 3836
- 24 Melguizo M, Nogueras M, Sanchez A. Synthesis 1992; 491
- 25 Rusinov GL, Gorbunov EB, Charushin VN, Chupakhin ON. Tetrahedron Lett. 2007; 48: 5873
- 26 Januar LA, Molinski TF. Org. Lett. 2013; 15: 2370
- 27 CCDC 1988314 (2b) and CCDC 1988315 (6i) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.