A Novel Entry into a New Class of (Chromanone-pyrrolidine/pyrrolizidine/pyrrolo[1,2-c]thiazole/pyrrolo[1,2-a]isoquinoline)indane-1,3-dione Ring Systems­ through [3+2] Cycloaddition

Abstract

A highly regioselective synthesis of novel dispiroheterocycles by the cycloaddition of azomethine ylide generated through a decarboxylative route from sarcosine/proline/thiazolidine-4-carboxylic­ acid/1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and ninhydrin with the dipolarophile 3-arylidene-4-chromanone is described.

Key words

1,3-dipole - chromanone - ninhydrin - pyrrolidine - pyrrolizidine

References

• 1 Tsuge O. Kanemasa S. Adv. Heterocycl. Chem.  1989,  45:  231 
• 2 1,3-Dipolar Cycloaddition Chemistry   Vol. 1-2:  Padwa A. Wiley; New York: 1984. 
• 3 Grigg R. Sridharan V. In Advances in Cycloaddition   Vol.3:  Curran DP. Jai Press; London: 1993.  p.161 
• 4a Daly JW. Spande TW. Whittaker N. Highet RJ. Feigl D. Noshimori N. Tokuyama T. Meyers CW. J. Nat. Prod.  1986,  46:  210 
• 4b Waldmann H. Synlett  1995,  133 
• 5 Molineux RJ. In Alkaloids: Chemical and Biological Perspectives   Pelletier SW. Wiley; New York: 1987.  Chap. 1.
• 6 Fujimori S. inventors; Jpn. Pat. Appl.  88-2912.  ; Chem. Abstr. 1990, 112, 98409
• 7 Kozikowski AP. Acc. Chem. Res.  1984,  17:  410 
• 8 Howe RK. Shelton BR. J. Org. Chem.  1990,  55:  4603 
• 9 De Amici M. de Michelli C. Sani VM. Tetrahedron  1990,  46:  1975 
• 10 Cohen VL, and Kleinman EE. inventors; PCT Int. Appl. WO  1995,24,398.  ; Chem. Abstr. 1995, 122, 20667j
• 11a Caroll WA. Grieco PA. J. Am. Chem. Soc.  1993,  115:  1164 
• 11b Early WG. Oh T. Overman LE. Tetrahedron Lett.  1988,  29:  3785 
• 11c Ban Y. Taga N. Oishi T. Chem. Pharm. Bull.  1976,  24:  736 
• 11d Ban Y. Seto M. Oishi T. Chem. Pharm. Bull.  1975,  23:  2605 
• 12a Ban Y. Taga N. Oishi T. Tetrahedron Lett.  1974,  187 
• 12b Van Tamlen EE. Yardley JP. Miyano M. Hinshaw WB. J. Am. Chem. Soc.  1969,  26:  7333 
• 13 Taylor PB. Culp JS. Debouck DC. Johnson RK. Patil AD. Woolf DJ. Brooks I. Herzberg RP. J. Biol. Chem.  1994,  269:  6325 
• 14 Crowther J. Hower R. Rao BS. Turner RW. J. Med. Chem.  1972,  15:  260 
• 15 Crutze J. Thomas K. Jerchal DS. Afr. Pat. 1968,6808,173, 1968,  Chem. Abstr. 1970, 72, 90290
• 16a Shanmugasundaram M. Arulananda Babu A. Raghunathan R. Padmamalar EJ. Heteroat. Chem.  1999,  10:  3316 
• 16b Shanmugasundaram M. Raghunathan R. Bhanumathi S. Padmamalar EJ. Heteroat. Chem.  1998,  9:  327 
• 16c Shanmugasundaram M. Raghunathan R. Tetrahedron  2000,  56:  5241 
• 17a Manikandan S. Shanmugasundaram M. Raghunathan R. Malar EJP. Heterocycles  2000,  53:  579 
• 17b Manikandan S. Ashraf MM. Raghunathan R. Synth. Commun.  2001,  31:  3593 
• 17c Manikandan S. Raghunathan R. J. Chem. Res., Synop.  2001,  424 
• 17d Manikandan S. Jayashankaran J. Raghunathan R. Synth. Commun.  2003,  33:  4059 
• 18a Jayashankaran J. Manikandan S. Raghunathan R. Synth. Commun.  2003,  33:  499 
• 18b Subramaniyan G. Raghunathan R. Tetrahedron  2001,  57:  2909 
• 18c Amalraj A. Raghunathan R. Tetrahedron  2001,  57:  10293 
• 18d Subramaniyan G. Raghunathan R. Castro M. Ana M. Synthesis  2002,  2440 
• 19a Grigg R. Surendrakumar S. Thianpatanagul S. Vipond D. J. Chem. Soc., Perkin Trans 1  1988,  2693 
• 19b Grigg R. Idle J. Mc Meekin P. Vipond D. J. Chem. Soc., Perkin Trans 1  1988,  2703 
• 19c Ding K. Wang G. Deschamps JR. Parrish DA. Wang S. Tetrahedron Lett.  2005,  46:  5949 
• 19d Onishi T. Sebahar PR. Williams RM. Org. Lett.  2003,  5:  3135 
• 19e Albrecht BK. Williams RM. Org. Lett.  2003,  5:  197 
• 19f Ahrendt KA. Williams RM. Org. Lett.  2004,  6:  4539 
• 19g Sebahar PR. Williams RM. J. Am. Chem. Soc.  2000,  122:  5666 
• 20 Bennett B. Donnelly JA. Meanney DC. Boyle PO. J. Chem. Soc., Perkin Trans 1  1972,  1554 
• 21 Fokas D. Ryan WJ. Casebier DS. Coffen D. Tetrahedron Lett.  1998,  39:  2235 
• 22 Crystal data: Molecular formula: C₂₈H₂₃NO₄, F_w = 437.47, block, colourless, size: 0.24 × 0.22 × 0.20 mm, triclinic, space group PI, a = 8.0652 (6) Å, b = 8.2977 (6) Å, c = 18.4090 (13) Å, α = 80.057 (1)°, β = 84.796 (1)°, γ = 69.754 (1)°, V = 1137.86 (14) ų, θ = 2.4-23.8°, T = 273 (2) K, Z = 2, D _r = 1.277 Mg m^-1, µ = 0.09 mm^-1. Data were collected on a Bruker SMART APEX CCD area-detector diffractometer (M_o-K _α radiation), cell parameters from 4856 reflections, 13219 measured reflections, 5232 independent reflections, 4501 reflections with I>2σ (I). R _int = 0.017; ω scans: -10 £ h £ 10, -10 £ k £ 10, -23 £ l £ 23. Further details on the crystal data is available in: Selvavinayagam S. Velmurugan D. Ravikumar K. Jayashankaran J. Raghunathan R. Acta Cryst., Sect. E  2005,  61:  o1582 
• 23a Govind MM. Selvavinayagam S. Velmurugan D. Ravikumar K. Suresh Babu AR. Raghunathan R. Acta Cryst., Sect. E  2004,  60:  54 
• 23b Govind MM. Selvavinayagam S. Velmurugan D. Ravikumar K. Suresh Babu AR. Raghunathan R. Acta Cryst., Sect. E  2004,  60:  57