Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2017; 28(11): 1315-1320
DOI: 10.1055/s-0036-1588757
DOI: 10.1055/s-0036-1588757
letter
l-Proline-Catalyzed Cyclization of 6-Aminopyrimidine-4(3H)-ones with Nitroolefins: Synthesis of Polysubstituted 5-Arylpyrrolo[2,3-d]pyrimidin-4-ones
Further Information
Publication History
Received: 04 January 2017
Accepted after revision: 26 February 2017
Publication Date:
13 March 2017 (online)
Abstract
A simple and efficient one-pot procedure for the synthesis of new pyrrolo[2,3-d]pyrimidine derivatives has been established through an l-proline-catalyzed cyclization of 6-aminopyrimidine-4(3H)-one with nitroolefins in water. The reaction at 80 °C in water gives various highly substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. This procedure has the advantages of environmental friendliness, good yields, and convenient operation.
-
References
- 1a Battaglia U, Long JE, Searle MS, Moody CJ. Org. Biomol. Chem. 2011; 9: 2227-2227
- 1b Loomis CR, Bell RM. J. Biol. Chem. 1988; 263: 1682-1682
- 1c Wu RT, Okabe T, Namikoshi M, Okuda S, Nishimura T, Tanaka N. J. Antibiot. (Tokyo) 1982; 35: 279-279
- 2a Golani LK, George C, Zhao S, Raghavan S, Orr S, Wallace A, Wilson MR, Hou Z, Matherly LH, Gangjee A. J. Med. Chem. 2014; 57: 8152-8152
- 2b Shen M, Zhou S, Li Y, Li D, Hou T. Mol. BioSyst. 2013; 9: 2435-2435
- 2c Ghorab MM, Ragab FA, Heiba HI, Youssef HA, El-Gazzar MG. Bioorg. Med. Chem. Lett. 2010; 20: 6316-6316
- 2d Clark MP, George KM, Bookland RG, Chen J, Laughlin SK, Thakur KD, Lee WL, Davis JR, Cabrera EJ, Brugel TA, Vanrens JC, Laufersweiler MJ, Maier JA, Sabat MP, Golebiowski A, Easwaran V, Webster ME, De B, Zhang G. Bioorg. Med. Chem. Lett. 2007; 17: 1250-1250
- 2e Gangjee A, Zhao Y, Raghavan S, Ihnat MA, Disch BC. Bioorg. Med. Chem. 2010; 18: 5261-5261
- 2f Wang L, Cherian C, Desmoulin SK, Mitchell-Ryan S, Hou Z, Matherly LH, Gangjee A. J. Med. Chem. 2012; 55: 1758-1758
- 2g Ding S, Wu TY. H, Brinker A, Peters EC, Hur W, Gray NS, Schultz PG. Proc. Natl. Acad. Sci. U.S.A. 2003; 100: 7632-7632
- 2h Wang Y, Mitchell-Ryan S, Raghavan S, George C, Orr S, Hou Z, Matherly LH, Gangjee A. J. Med. Chem. 2015; 58: 1479-1479
- 3a Prieur V, Heindler N, Rubio-Martínez J, Guillaumet G, Pujol MD. Tetrahedron 2015; 71: 1207-1207
- 3b Dodonova J, Skardziute L, Kazlauskas K, Jursenas S, Tumkevicius S. Tetrahedron 2012; 68: 329-329
- 3c Vrábel M, Pohl R, Votruba I, Sajadi M, Kovalenko SA, Ernsting NP, Hocek M. Org. Biomol. Chem. 2008; 6: 2852-2852
- 3d Tumkevicius S, Dodonova J. Synlett 2011; 1705-1705
- 3e Tumkevicius S, Dodonova J, Kazlauskas K, Masevicius V, Skardziute L, Jursenas S. Tetrahedron Lett. 2010; 51: 3902-3902
- 4a Rashad AE, Mohamed MS, Zaki ME. A, Fatahala SS. Arch. Pharm. (Weinheim, Ger.) 2006; 339: 664-664
- 4b Saxena NK, Hagenow BM, Genzlinger G, Turk SR, Drach JC, Townsend LB. J. Med. Chem. 1988; 31: 1501-1501
- 4c Varaprasad CV. N. S, Ramasamy KS, Girardet J.-L, Gunic E, Lai V, Zhong W, An H, Hong Z. Bioorg. Chem. 2007; 35: 25-25
- 4d Pudlo JS, Saxena NK, Nassiri MR, Turk SR, Drach JC, Townsend LB. J. Med. Chem. 1988; 31: 2086-2086
- 5 Mohamed MS, Kamel R, Abd El-hameed RH. Med. Chem. Res. 2013; 22: 2244-2244
- 6a Wang L, Desmoulin SK, Cherian C, Polin L, White K, Kushner J, Fulterer A, Chang M.-H, Mitchell-Ryan S, Stout M, Romero MF, Hou Z, Matherly LH, Gangjee A. J. Med. Chem. 2011; 54: 7150-7150
- 6b Wang Y, Cherian C, Orr S, Mitchell-Ryan S, Hou Z, Raghavan S, Matherly LH, Gangjee A. J. Med. Chem. 2013; 56: 8684-8684
- 6c Wang L, Cherian C, Desmoulin SK, Polin L, Deng Y, Wu J, Hou Z, White K, Kushner J, Matherly LH, Gangjee A. J. Med. Chem. 2010; 53: 1306-1306
- 6d Golani LK, Wallace-Povirk A, Deis SM, Wong J, Ke J, Gu X, Raghavan S, Wilson MR, Li X, Polin L, Waal PW, White K, Kushner J, O’Connor C, Hou Z, Xu HE, Melcher K, Dann CE, Matherly LH, Gangjee A. J. Med. Chem. 2016; 59: 7856-7856
- 7 Desmoulin SK, Wang L, Hales E, Polin L, White K, Kushner J, Stout M, Hou Z, Cherian C, Gangjee A, Matherly LH. Mol. Pharmacol. 2011; 80: 1096-1096
- 8a Trzoss M, Bensen DC, Li X, Chen Z, Thanh L, Zhang J, Creighton CJ, Cunningham ML, Kwan B, Stidham M, Nelson K, Brown-Driver V, Castellano A, Shaw KJ, Lightstone FC, Wong SE, Nguyen TB, Finn J, Tari LW. Bioorg. Med. Chem. Lett. 2013; 23: 1537-1537
- 8b Hilmy KM. H, Khalifa MM. A, Hawata MA. A, Keshk RM. A. A, El-Torgman AA. Eur. J. Med. Chem. 2010; 45: 5243-5243
- 8c Mohamed MS, Kamel R, Fatahala SS. Eur. J. Med. Chem. 2011; 46: 3022-3022
- 9a El-Gaby MS. A, Gaber AM, Atalla AA, Abd Al-Wahab KA. Farmaco 2002; 57: 613-613
- 9b Tumkevicius S, Urbonas A, Vainilavicius P. Chem. Heterocycl. Compd. (N. Y., NY U. S.) 2000; 36: 841-841
- 10a Gangjee A, Namjoshi OA, Ihanat MA, Buchanan A. Bioorg. Med. Chem. Lett. 2010; 20: 3177-3177
- 10b Gangjee A, Zaware N, Raghavan S, Yang J, Thorpe JE, Ihanat MA. Bioorg. Med. Chem. 2012; 20: 2444-2444
- 10c Kumar VP, Frey KM, Wang Y, Jain HK, Gangjee A, Anderson KS. Bioorg. Med. Chem. Lett. 2013; 23: 5426-5426
- 11 Chattopadhyay S, Moran RG, Goldman ID. Mol. Cancer Ther. 2007; 6: 404-404
- 12a Motsuoka M. J. Antibiot., Ser. A 1960; 13: 121-121
- 12b Yen L, Magnier M, Weissleder R, Stockwell BR, Mulligan R. RNA 2006; 12: 797-797
- 13a Miwa T, Hitaka T, Akimoto H. J. Org. Chem. 1993; 58: 1696-1696
- 13b Taylor EC, Mao Z. J. Org. Chem. 1996; 61: 7973-7973
- 13c Taylor EC, Patel HH, Jun J.-G. J. Org. Chem. 1995; 60: 6684-6684
- 14a Cheng H, Johnson TO. Jr, Kath JC, Liu KK.-C, Lunney EA, Nagata A, Nair SK, Planken SP, Sutton SC. WO 2013042006, 2013
- 14b Cheng H, Nair SK, Murray BW, Almaden C, Bailey S, Baxi S, Behenna D, Cho-Schultz S, Dalvie D, Dinh DM, Edwards MP, Li FJ, Ferre RA, Gajiwala KS, Hemkens MD, Jackson-Fisher A, Jalaie M, Johnson TO, Kania RS, Kephart S, Lafontaine J, Lunney B, Liu KK.-C, Liu Z, Matthews J, Nagata A, Niessen S, Ornelas MA, Orr ST. M, Pairish M, Planken S, Ren S, Richter D, Ryan K, Sach N, Shen H, Smeal T, Solowiej J, Sutton S, Tran K, Tseng E, Vernier W, Walls M, Wang S, Weinrich SL, Xin S, Xu H, Yin M.-J, Zientek M, Zhou R, Kath JC. J. Med. Chem. 2016; 59: 2005-2005
- 15a Sekhar NM, Acharyulu PV. R, Anjaneyulu Y. Tetrahedron Lett. 2011; 52: 4140-4140
- 15b De Coen LM, Heugebaert TS. A, Garcia D, Stevens CV. Chem. Rev. 2016; 116: 80-80
- 15c Tumkevicius S, Dodonova J. Chem. Heterocycl. Compd. (N. Y., NY U. S.) 2012; 48: 258- 258
- 16a Mayasundari A, Fujii N. Tetrahedron Lett. 2010; 51: 3597-3597
- 16b Prieur V, Rubio-Martínez J, Font-Bardia M, Guillaumet G, Pujol MD. Eur. J. Org. Chem. 2014; 1514-1514
- 16c Jiang X, Sun D, Jiang Y, Ma D. Tetrahedron Lett. 2015; 56: 3259-3259
- 17 Taylor ED, Liu B. J. Org. Chem. 2003; 68: 9938-9938
- 18 Saikia L, Roudragouda P, Thakur AJ. Bioorg. Med. Chem. Lett. 2016; 26: 992-992
- 19a Wang Y, Shang Z.-c, Wu T.-x, Fan J.-c, Chen X. J. Mol. Catal. A: Chem. 2006; 253: 212-212
- 19b Srinivasan M, Perumal S, Selvaraj S. ARKIVOC 2005; (xi): 201-201
- 19c Dodda R, Zhao CG. Synthesis 2006; 3238-3238
- 19d He Y.-H, Cao J.-F, Li R, Xiang Y, Yang D.-C, Guan Z. Tetrahedron 2015; 71: 9299-9299
- 20a Zhang F, Li C, Qi C. Synthesis 2013; 45: 3007-3007
- 20b Li C, Liang X, Zhang F, Qi C. Catal. Commun. 2015; 62: 6-6
- 20c Zhang F, Li C, Wang C, Qi C. Org. Biomol. Chem. 2015; 13: 5022-5022
- 20d Chen Z, Shi Y, Shen Q, Xu H, Zhang F. Tetrahedron Lett. 2015; 56: 4749-4749 ; highlighted in Synfacts 2015, 11, 1118
- 20e Li C, Zhang F, Yang Z, Qi C. Tetrahedron Lett. 2014; 55: 5430-5430
- 20f Li C, Zhang F. RSC Adv. 2016; 6: 75359-75359
- 20g Li C, Zhang F, Qi C. RSC Adv. 2016; 6: 102924-102924
- 21 2-Amino-5-aryl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-ones 3; General Procedure A mixture of 2,6-diaminopyrimidin-4(3H)-one (1, 0.5 mmol), the appropriate nitroolefin 2 (0.5 mmol), and l-proline (10 mol%) in H2O (2.5 mL) was heated at 80 °C for the appropriate time then cooled to r.t. The mixture was diluted with cold H2O (30 mL), and the solid was collected by filtration, washed with H2O and 95% EtOH, dried, and crystallized from 95% EtOH to give the pure product 3.
- 22 2-Amino-5-(4-methoxyphenyl)-6-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (3f) Prepared by following the general procedure from 2,6-diaminopyrimidin-4(3H)-one (1, 0.5 mmol) and 1-methoxy-4-[(1E)-2-nitroprop-1-en-1-yl]benzene (0.5 mmol) as a pale-yellow solid; yield: 104.5 mg (77%); mp >300 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 10.94 (s, 1 H, NH), 10.16 (s, 1 H, NH), 7.33 (d, J = 8.0 Hz, 2 H, ArH), 6.88 (d, J = 8.4 Hz, 2 H, ArH), 6.00 (br s, 2 H, NH2), 3.76 (s, 3 H, OMe), 2.17 (s, 3 H, CH3). 13C NMR (100 MHz, DMSO-d 6): δ = 158.9, 157.4, 152.3, 151.1, 131.3, 127.6, 123.0, 113.2, 98.0, 55.4, 12.1. HRMS (ESI): m/z [M + H]+ calcd for C14H15N4O2 +: 271.1190; found: 271.1194.