Synlett 2013; 24(15): 1973-1977
DOI: 10.1055/s-0033-1338965
letter
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of Novel Glycosyl Oxindoles through 1,3-Dipolar Cyclo­addition

N. Sirisha
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, India   Fax: +91(44)22300488   Email: [email protected]
,
R. Raghunathan*
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, India   Fax: +91(44)22300488   Email: [email protected]
› Author Affiliations
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.

 
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  • 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.
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