Novel Syntheses of N-Aryloxazolidin-2-ones via Tandem Reactions of Vinyl Sulfonium Salts

Abstract

An unprecedented and efficient domino reaction of diphenyl vinyl sulfonium salt with carbamates leading to the syntheses of N-aryloxazolidin-2-ones has been developed. The scope of this transformation has been studied and a plausible mechanism has been proposed.

N-aryloxazolidin-2-one - tandem reaction - vinyl sulfonium - carbamate

References and Notes

1a Mukhtar TA. Wright GD. Chem. Rev.  2005,  105:  529 

1b Brickner SJ. Curr. Pharm. Des.  1996,  2:  175 

2a Tucker JA. Allwine DA. Grega KC. Barbachyn MR. Klock JL. Adamski JL. Brickener SJ. Hutchinson DK. Ford CW. Zurenko GE. Conradi RA. Burton PS. Jensen RM. J. Med. Chem.  1998,  41:  3727 

2b Genin MJ. Hutchinson DK. Allwine DA. Hester JB. Hemmert DE. Garmon SA. Ford CW. Zurenko GE. Hamel JC. Schaadt RD. Stapert D. Yagi BH. Friis JM. Shobe EM. Adams WJ. J. Med. Chem.  1998,  41:  5144 

2c Gleave DM. Brickner SJ. Manninen PR. Allwine DA. Lovasz KD. Rohrer DC. Tucker JA. Zurenko GE. Ford CW. Bioorg. Med. Chem. Lett.  1998,  8:  1231 

2d Brickner SJ. Hutchinson DK. Barbachyn MR. Manninen PR. Ulanowicz DA. Garmon SA. Grega KC. Hendges SK. Toops DS. Ford CW. Zurenko GE. J. Med. Chem.  1996,  39:  673 

2e Gleave DM. Brickner SJ. J. Org. Chem.  1996,  61:  6470 

3 Ali A. Reddy GSKK. Cao H. Anjum SG. Nalam MNL. Schiffer CA. Rana TM. J. Med. Chem.  2006,  49:  7342 

4a Burke CP. Shu L.-H. Shi Y.-A. J. Org. Chem.  2007,  72:  6320 

4b Shu L.-H. Wang P.-Z. Gan Y.-H. Shi Y.-A. Org. Lett.  2003,  5:  293 

4c Poindexter GS. Owens DA. Dolan PL. Woo E. J. Org. Chem.  1992,  57:  6257 

5a Nicolaou KC. Zhong Y.-L. Baran PS. Angew. Chem. Int. Ed.  2000,  39:  625 

5b Jegham S. Nedelec A. Burnier P. Guminski Y. Puech F. Koenig JJ. George P. Tetrahedron Lett.  1998,  39:  4453 

5c Schaus SE. Jacobsen EN. Tetrahedron Lett.  1996,  37:  7937 

6a Brickner SJ. Hutchinson DK. Barbachyn MR. Manninen PR. Ulanowicz DA. Garmon SA. Grega KC. Hendges SK. Toops DS. Ford CW. Zurenko GE. J. Med. Chem.  1996,  39:  673 

6b Griera R. Cantos-Llopart C. Amat M. Bosch J. Del Castillob JC. Huguet J. Bioorg. Med. Chem. Lett.  2005,  15:  2515 

6c Perrault WR. Pearlman BA. Godrej DB. Jeganathan A. Yamagata K. Chen J.-J. Lu CV. Herrinton PM. Gadwood RC. Chan L. Lyster MA. Maloney MT. Moeslein JA. Greene ML. Barbachyn MR. Org. Process Res. Dev.  2003,  7:  533 

7a Ghosh A. Sieser JE. Riou M. Cai W. Rivera-Ruiz L. Org. Lett.  2003,  5:  2207 

7b Cacchi S. Fabrizi G. Goggiamani A. Zappia G. Org. Lett.  2001,  3:  2539 

7c Moreno-Mañas M. Morral L. Pleixats R. Villarroya S. Eur. J. Org. Chem.  1999,  181 

7d Larksarp C. Alper H. J. Am. Chem. Soc.  1997,  119:  3709 

7e Trost B. Sudhakar AR. J. Am. Chem. Soc.  1988,  110:  7933 

8a Ghosh A. Sieser JE. Caron S. Couturier M. Dupont-Gaudet K. Girardin M. J. Org. Chem.  2006,  71:  1258 

8b Mallesham B. Rajesh BM. Rajmohan Reddy P. Srinivas D. Trehan S. Org. Lett.  2003,  5:  963 

9a Yamanaka H. Yamane Y. Mukaiyama T. Heterocycles  2004,  63:  2813 

9b Matsuo J. Yamanaka H. Kawana A. Mukaiyama T. Chem. Lett.  2003,  32:  392 

9c Rowbottom MW. Mathews N. Gallagher T. J. Chem. Soc., Perkin Trans. 1  1998,  3927 

9d Garst ME. Arrhenius P. J. Org. Chem.  1983,  48:  19 

9e Braun H. Huber G. Tetrahedron Lett.  1976,  17:  2121 

10 Wang YF. Zhang WH. Colandrea VJ. Jimenez LS. Tetrahedron  1999,  55:  10659 

11 Kim KH. Jimenez LS. Tetrahedron: Asymmetry  2001,  12:  999 

12a Yar M. McGarrigle EM. Aggarwal VK. Org. Lett.  2009,  11:  257 

12b Yar M. McGarrigle EM. Aggarwal VK. Angew. Chem. Int. Ed.  2008,  47:  3784 

12c Unthank MG. Tavassoli B. Aggarwal VK. Org. Lett.  2008,  10:  1501 

12d Unthank MG. Hussain N. Aggarwal VK. Angew. Chem. Int. Ed.  2006,  45:  7066 

13a Campbell AL. Lenz GR. Synthesis  1987,  421 

13b Robiette R. Cheboub-Benchaba K. Peeters D. Marchand-Brynaert J. J. Org. Chem.  2003,  68:  9809 

13c Nguyen TB. Martel A. Dhal R. Dujardin G. J. Org. Chem.  2008,  73:  2621 

14

Typical Procedure for the Tandem Reactions - Synthesis of 3-Phenyloxazolidin-2-one
tert-Butyl phenylcarbamate (96 mg, 0.5 mmol) and Et₃N (152 mg, 1.5 mmol) were charged into an oven-dried flask, followed by the addition of CH₂Cl₂ (2 mL) under the protection of nitrogen atmosphere to form a solution. The solution of diphenyl vinyl sulfonium triflate (543 mg, 1.5 mmol) in CH₂Cl₂ (3 mL) was added into the above solution by syringe under N₂ at r.t. The reaction mixture was then put into a 45 ˚C oil bath to react for 24 h. After the completion of reaction, the solvent was removed under reduced pressure. The residue was then separated on a silica gel column by using PE-EtOAc (1:2) as eluent, and the final product was obtained as pale yellow powder (42 mg, 52%). ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 7.51 (d, J = 8.0 Hz, 2 H), 7.36 (t, J = 8.0 Hz, 2 H), 7.12 (t, J = 7.4 Hz, 1 H), 4.42 (t, J = 8.0 Hz, 2 H), 3.99 (t, J = 8.0 Hz, 2 H). ^¹³C NMR (100 MHz, CDCl₃): δ = 155.3, 138.3, 129.1, 124.1, 118.2, 61.3, 45.2. HRMS (EI): m/z calcd for C₉H₉NO₂ [M]⁺: 163.0633; found: 163.0627.