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 2013; 24(15): 1973-1977
DOI: 10.1055/s-0033-1338965
DOI: 10.1055/s-0033-1338965
letter
Facile Synthesis of Novel Glycosyl Oxindoles through 1,3-Dipolar Cycloaddition
Further Information
Publication History
Received: 18 April 2013
Accepted after revision: 27 June 2013
Publication Date:
13 August 2013 (online)
Abstract
Synthesis of a series of glycosyl spirooxindoles has been accomplished through an intermolecular 1,3-dipolar cycloaddition reaction of an azomethine ylide generated from glucose with the dipolarophile 4-(E)-3-phenacylidene oxindole.
-
References and Notes
- 1a Ding K, Lu Y, Nikolovska-Coleska Z, Qiu S, Ding Y, Gao W, Stuckey J, Krajewski K, Roller PP, Tomita Y, Parrish DA, Deschamps JR, Wang S. J. Am. Chem. Soc. 2005; 127: 10130
- 1b Ding K, Lu Y, Nikolovska-Coleska Z, Wang G, Qiu S, Shangary S, Gao W, Qin D, Stuckey J, Krajewski K, Roller PP, Wang S. J. Med. Chem. 2006; 49: 3432
- 2a Basavaiah D, Reddy KR. Org. Lett. 2007; 9: 57
- 2b Miyamoto H, Okawa Y, Nakazaki A, Kobayashi S. Angew. Chem. Int. Ed. 2006; 45: 2274
- 2c Nair V, Vellalath S, Poonoth M, Mohan R, Suresh E. Org. Lett. 2006; 8: 507
- 2d Ding K, Lu Y, Nikolovska-Coleska Z, Wang G, Qiu S, Shangary S, Gao W, Qin D, Stuckey J, Krajewski K, Roller PP, Wang S. J. Med. Chem. 2006; 49: 3432
- 2e Teng Zhang H, Mendonca A. Molecules 2006; 11: 700
- 2f Lo MM. C, Neumann CS, Nagayama S, Perlstein EO, Schreiber SL. J. Am. Chem. Soc. 2004; 126: 16077
- 3a Huang A, Kodanko JJ, Overman LE. J. Am. Chem. Soc. 2004; 126: 14043
- 3b Bagul TD, Lakshmaiah G, Kawabata T, Fuji K. Org. Lett. 2002; 4: 249
- 3c Dounay AB, Overman LE. Chem. Rev. 2003; 103: 2945
- 3d Trost BM, Frederiksen MU. Angew. Chem. 2005; 117: 312
- 3e Yong SR, Willams MC, Pyne SG, Ung AT, Skelton BW, White AH, Turner P. Tetrahedron 2005; 61: 8120
- 3f Beccalli EM, Cleriici F, Gelmi ML. Tetrahedron 2003; 59: 4615
- 3g Kawasaki T, Ogawa A, Terashima R, Saheki T, Ban N, Sekiguchi H, Sakaguchi K, Sakamoto M. J. Org. Chem. 2005; 70: 2957
- 4a Pandey G, Banerjee P, Gadre SR. Chem. Rev. 2006; 106: 4484
- 4b Coldham I, Hufton R. Chem. Rev. 2005; 105: 2765
- 4c Gu YG, Xu Y, Krueger AC, Madigan D, Sham HL. Tetrahedron Lett. 2002; 43: 955
- 4d Rehn S, Bergman J, Stensland B. Eur. J. Org. Chem. 2004; 413
- 4e Sebahar PR, Osada H, Usui T, Williams RM. Tetrahedron 2002; 58: 6311
- 4f Belfaitah A, Isly M, Carboni B. Tetrahedron Lett. 2004; 45: 1969
- 4g Praveen C, Sagayaraj YW, Perumal PT. Tetrahedron Lett. 2009; 50: 644
- 4h Suresh Babu AR, Raghunathan R, Baskaran S. Tetrahedron 2009; 65: 2239
- 4i Kawashima K, Kakehi A, Noguchi M. Tetrahedron 2007; 63: 1630
- 4j Yan X, Peng Q, Zhang K, Hong W, Hou X, Wu Y. Angew. Chem. 2006; 118: 2013
- 4k Lukoyanova O, Cardona CM, Altable M, Filippone S, Domenech AM, Martin N, Echegoyen L. Angew. Chem. 2006; 118: 7590
- 4l Mamane V, Riant O. Tetrahedron 2001; 57: 2555
- 4m Jayashankaran J, Manian RD. R. S, Raghunathan R. Synthesis 2006; 1028
- 4n Boruah M, Konwar D, Sharma SD. Tetrahedron Lett. 2007; 48: 4535
- 5a Shanmugam P, Viswambharan B, Suchithra M. Org. Lett. 2007; 9: 4095
- 5b Viramgama P. Ind. J. App. Res. 2012; 2: 2249
- 6 Doddi VR, Kokatla HP, Pal AP. J, Basak RK, Vankar YD. Eur. J. Org. Chem. 2008; 5731
- 7 Calarese DA, Scanlan CN, Zwick MB, Deechongkit S, Mimura Y, Kunert R, Zhu P, Wormald MR, Stanfield RL, Roux KH, Kelly JW, Rudd PM, Dwek RA, Katinger H, Burton DR, Wilson IA. Science 2003; 300: 2065
- 8 Ferguson NM, Cummings DA. T, Cauchemez S, Fraser C, Riley S, Meeyai A, Iamsirithaworn S, Burke DS. Nature 2005; 437: 209
- 9 Jianglong Z, Warren JD, Danishefsky SJ. Expert Rev. Vacc. 2009; 8: 1399
- 10 Martínez-Monteroa S, Fernández S, Sanghvi YS, Theodorakis EA, Detorio MA, Mcbrayer TR, Whitaker T, Schinazi RF, Vicente G, Ferreroa M. Bioorg. Med. Chem. 2012; 20: 6885
- 11 Dixit Y, Dixit R, Gautam N, Gautam DC. Nucleosides Nucleotides Nucleic Acids 2009; 28: 998
- 12a Arumugam N, Raghunathan R. Tetrahedron 2010; 66: 969
- 12b Rajesh R, Raghunathan R. Tetrahedron Lett. 2010; 51: 5845
- 12c Prasanna R, Purushothaman S, Suresh M, Raghunathan R. Tetrahedron Lett. 2011; 52: 792
- 12d Rao JN. S, Raghunathan R. Tetrahedron Lett. 2012; 53: 854
- 13 Dandia A, Sati M, Arya K, Sharma R, Loupy A. Chem. Pharm. Bull. 2003; 51: 1137
- 14 Xavier NM, Rauter AP. Carbohydr. Res. 2008; 343: 1523
- 15 Representative Procedure for the Synthesis of Glycosyl Spirooxindolo Pyrrolidines: To a solution of O-benzyl-protected sugar aldehyde 3 (1 mmol), sarcosine (2; 1 mmol) in anhyd toluene (25 mL), 4-(E)-3-phenacylidene oxindole 1a/b (1 mmol) was added and the mixture was heated to reflux for 5–8 h using a Dean–Stark apparatus. After the completion of reaction (TLC), toluene was evaporated under reduced pressure and the residue was purified by column chromatography using hexane–EtOAc (9:1) as eluent. Spectral Data of Compound 5a: pale yellow liquid. IR (KBr): 1682, 1703 cm–1. 1H NMR (300 MHz, CDCl3): δ = 1.42 (br s, 10 H), 2.43 (s, 3 H), 2.75 (t, J = 9.6 Hz, 1 H), 3.46 (s, 1 H), 4.12 (dd, J = 9.6, 3.9 Hz, 1 H), 4.48 (dd, J = 9.6, 3.9 Hz, 1 H), 4.60 (dd, J = 5.4, 2.4 Hz, 1 H), 4.91 (d, J = 2.4 Hz, 1 H), 5.23 (d, J = 5.4 Hz, 1 H), 6.29 (d, J = 7.8 Hz, 1 H), 6.77–7.29 (m, 8 H), 7.71 (s, 1 H). 13C NMR (75 MHz, CDCl3): δ = 23.56, 23.95, 24.86, 37.0, 37.44, 41.26, 52.29, 55.93, 60.29, 72.72, 82.60, 100.56, 100.65, 105.45, 108.40, 113.01, 121.80, 122.42, 126.64, 127.82, 127.89, 128.11, 128.29, 132.44, 137.17, 140.21, 157.99, 178.74, 197.26. MS (ESI): m/z = 487.13 [M+ + 1]. Anal. Calcd for C29H30N2O5: C, 78.03; H, 5.73; N, 7.58. Found: C, 78.12; H, 5.81; N, 7.42.
- 16 Karthikeyan K, Senthil Kumar R, Muralidharan D, Perumal PT. Tetrahedron Lett. 2009; 50: 7175
For reviews, see: