Subscribe to RSS
DOI: 10.1055/s-2002-35982
Synthesis of Novel 2,3-Dihydroimidazo[2,1-b][1,3]oxazoles Through Intramolecular Nucleophilic ipso-Substitution in 2-Alkylsulfonylimidazoles
Publication History
Publication Date:
06 December 2002 (online)
Abstract
Readily available 2-(benzylsulfanyl)imidazoles 6, were studied as potential precursors toward the synthesis of novel diversely substituted 2,3-dihydroimidazo[2,1-b][1,3]oxazoles. Thus, the reaction between enolates derived from 6 and different electrophiles as well as the addition of Grignard reagents to the carbonyl group in 6 were explored. The formation of the fused imidazoxazoles 20 under mild conditions was successfully accomplished taking advantage of the key role played by the 2-alkylsulfonyl moiety in 19 as an efficient leaving group in intramolecular nucleophilic ipso-substitution reactions.
Key words
alkylsulfonyl groups - leaving groups - intramolecular nucleophilic ipso-substitution - imidazoles - 2,3-dihydroimidazo[2,1-b][1,3]oxazoles
- 1
Shepard RG.Fedrik JF. Adv. Heterocycl. Chem. 1965, 4: 145 - 2
Vecchietti V.Dredi E.Lauria F. J. Chem. Soc., C 1971, 2554 - 3
Franco F.Greenhouse R.Muchowski JM. J. Org. Chem. 1982, 47: 1682 - 4
Zumbrunn A. Synthesis 1998, 1357 - 5
Grimmett MR. Adv. Heterocycl. Chem. 1970, 12: 103 - 6
Grimmett MR. Adv. Heterocycl. Chem. 1980, 27: 241 - 7
Preston PN. Chem. Rev. 1974, 74: 279 - 8
Brown DJ.Ford PW. J. Chem. Soc. C 1967, 568 - 9
Barlin GB.Brown WV. J. Chem. Soc. C 1967, 2473 - 10
Heras M.Ventura M.Linden A.Villalgordo JM. Synthesis 1999, 1613 - 11
Jarosinski MA.Anderson WK. J. Org. Chem. 1991, 56: 4058 - 12
Obrecht D.Villalgordo JM. Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular Weight Compound Libraries, Tetrahedron Organic Chemistry Series Vol. 17: Pergamon; Oxford: 1998. - 13
Obrecht D.Grieder A.Abrecht C.Villalgordo JM. Helv. Chim. Acta 1997, 80: 65 - 14
Chucholowski A.Masquelin T.Obrecht D.Stadlwieser J.Villalgordo JM. Chimia 1996, 50: 525 - 15
Villalgordo JM. Methods Find. Exp. Clin. Pharmacol. 1997, 19 (Suppl. A): 37 - 16
Villalgordo JM.Obrecht D.Chucholowski A. Synlett 1998, 1405 - 17
Font D.Heras M.Villalgordo JM. Synthesis 2002, 1813 - 18
Kaminski JJ.Bristol JA.Puchalski C.Lovey RG.Elliot AJ.Guzik H.Solomon DM.Conn DJ.Domalski MS.Wong S.-C.Gold EH.Long JF.Chiu PJS.Steinberg M.McPhail AT. J. Med. Chem. 1985, 28: 876 - 19
Fos E.Bosca F.Mauleon D.Garganico G. J. Heterocycl. Chem. 1993, 30: 473 - 20
Stefancich G.Silvestri R.Artico M. J. Heterocycl. Chem. 1993, 30: 529 - 21
Shawcross A.Stanforth SP. J. Heterocycl. Chem. 1993, 30: 563 - 22
Aldabbagh F.Bowman WR. Tetrahedron Lett. 1993, 38: 3793 - 23
Aldabbagh F.Bowman WR.Mann E. Tetrahedron Lett. 1997, 38: 7937 - 24
Hua DH.Zhang F.Chen J.Robinson PD. J. Org. Chem. 1994, 59: 5084 - 25
Johnson CK. ORTEP II. Report ORNL-5138 Oak Ridge National Laboratory; Tennessee: 1976. - 27
Sheldrick GM. SHELXS-97, Program for Crystal Structure Solution University of Göttingen; Göttingen, Germany: 1997. - 28
Sheldrick GM. M. SHELXS-97, Program for the Refinement of Crystal Structures form Diffraction Data University of Göttingen; Göttingen, Germany: 1997.
References
Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC-187224 (Compound 24). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 122 3336033; e-mail: deposit@ccdc.cam.ac.uk).