Highly Efficient Construction of Sugar-Fused Spirochromanono Pyrrolidines/Pyrrolizidines/Thiolizidines via 1,3-Dipolar Cycloaddition of Azomethine Ylides

Abstract

A variety of sugar-fused chromanono pyrrolidines/pyrrolizidines/thiolizidines have been synthesized by intermolecular 1,3-dipolar cycloaddition reaction of azomethine ylides (generated from glucose aldehyde and different secondary amino acids) with various 3-arylidene chroman-4-ones as dipolarophiles. The solvent effect on the 1,3-dipolar cycloaddition reaction is also studied.

Key words

1,3-dipolar cycloaddition - spirochromanones - glycosyl heterocycles­ - azomethine ylide - pyrrolidines

• References and Notes

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• 21 Experimental procedure and characterization data for cycloadduct 5b: A solution of O-benzyl tethered sugar aldehyde 3 (0.1 g, 0.31 mmol), sarcosine 2 (0.028 g, 0.346 mmol) and 3-arylidene chroman-4-one 1b (0.088 g, 0.31 mmol) was heated to reflux in anhydrous toluene for 8 h. The crude product was purified by column chromatography (hexane/EtOAc, 99:1) to give 5b as a pale-yellow liquid (0.11 g, 66%). IR (KBr): 1342, 1520, 1690 cm^–1. ¹H NMR (CDCl₃, 300 MHz): δ = 1.49 (br s, 10 H), 2.40 (s, 3 H), 2.85 (t, J = 9.3 Hz, 1 H), 3.08 (dd, J = 3.6, 9.3 Hz, 1 H), 3.41 (dd, J = 3.6, 9.3 Hz, 1 H), 3.77 (s, 1 H), 3.93 (d, J = 12.3 Hz, 1 H), 4.27 (d, J = 12.3 Hz, 1 H), 5.09 (dd, J = 2.4, 5.4 Hz, 1 H), 5.14 (d, J = 2.4 Hz, 1 H), 5.91 (d, J = 5.4 Hz, 1 H), 6.69–8.07 (m, 8 H). ¹³C NMR (75 MHz): δ = 22.89, 22.91, 23.81, 35.94, 36.49, 39.27, 48.19, 57.51, 60.13, 64.48, 68.33, 81.31, 101.36, 104.74, 111.63, 116.50, 117.99, 120.59, 122.18, 122.77, 122.95, 127.30, 128.63, 129.44, 135.45, 146.06, 147.46, 157.43, 159.98, 192.08. MS (ESI); m/z = 519.1 [M⁺+1]. Anal. Calcd for C₂₉H₃₀N₂O₇: C, 67.17; H, 5.83; N, 5.40; found: C, 67.24; H, 5.81; N, 5.32
• 22 Karthikeyan K. Senthil KumarR. Muralidharan D. Perumal PT. Tetrahedron Lett. 2009; 50: 7175
• 23 Experimental procedure and characterization data for cycloadduct 11b: A solution of O-benzyl tethered sugar aldehyde 3 (0.1 g, 0.31 mmol), thiazolidine-4-carboxylic acid 10 (0.042 g, 0.346 mmol) and 3-arylidene chroman-4-one 1b (0.088 g, 0.31 mmol) was heated to reflux in anhydrous toluene for 8 h. The crude product was purified by column chromatography (hexane/EtOAc, 98:2) to give 11b as a pale-yellow liquid (0.12 g, 67%). IR (KBr): 1684, 1551, 1352 cm^–1. ¹H NMR (CDCl₃, 300 MHz): δ = 1.53 (br s, 10 H), 2.39 (dd, J = 5.1, 9.3 Hz, 1 H), 3.37 (dd, J = 5.1, 9.3 Hz, 1 H), 3.48 (d, J = 11.4 Hz, 1 H), 3.83 (s, 1 H), 4.05 (d, J = 3.6 Hz, 1 H), 4.11 (d, J = 11.4 Hz, 1 H), 4.23–4.28 (m, 1 H), 4.49 (d, J = 12 Hz, 1 H), 4.61 (d, J = 12 Hz, 1 H), 4.77 (dd, J = 2.4, 5.4 Hz, 1 H), 5.23 (d, J = 2.4 Hz, 1 H), 5.86 (d, J = 5.4 Hz, 1 H), 6.82–8.09 (m, 8 H). ¹³C NMR (75 MHz): δ = 23.57, 23.72, 24.69, 35.42, 37.26, 43.11, 44.10, 55.53, 58.68, 71.59, 71.69, 72.78, 82.74, 99.83, 104.32, 113.27, 117.78, 123.77, 125.90, 127.75, 128.21, 128.63, 129.65, 136.62, 136.98, 146.14, 153.34, 167.12, 194.70. MS (ESI); m/z = 563.3 [M⁺+1]. Anal. Calcd for C₃₀H₃₀N₂O₇S: C, 64.04; H, 5.37; N, 4.98; found: C, 64.12; H, 5.41; N, 4.87