Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2004(10): 1589-1594
DOI: 10.1055/s-2004-822391
DOI: 10.1055/s-2004-822391
PAPER
© Georg Thieme Verlag Stuttgart · New York
‘One-Pot’ Synthesis of Chiral N-Protected α-Amino Acid-Derived 1,2,4-Oxadiazoles
Further Information
Received
9 January 2004
Publication Date:
26 May 2004 (online)
Publication History
Publication Date:
26 May 2004 (online)
Abstract
A series of α-amino acid-derived 1,2,4-oxadiazoles have been synthesized via an easy, inexpensive and one-pot protocol. The heterocycles were obtained in good yields and in relatively short reaction times.
Key words
amino acids - oxadiazoles - heterocycles
-
1a
Luthman K.Borg S.Hacksell O. Methods Mol. Med. 1999, 23: 1 -
1b
Andersen KE.Jorgensen AS.Braestrup C. Eur. J. Med. Chem. 1994, 29: 393 - 2
Clapp LB. Adv. Heterocycl. Chem. 1976, 65 - 3
Orlek BS.Blaney FE.Brown F.Clark MSG.Hadley MS.Hatcher J.Riley GJ.Rosenborg HE.Wadsworth HJ.Wyman P. J. Med. Chem. 1991, 34: 2726 - 4
Watjen F.Baker R.Engelstoff M.Herbert R.MacLeod A.Knight A.Merchant K.Moseley J.Saunders J.Swain C.Wong E.Springer JP. J. Med. Chem. 1989, 32: 2282 - 5
Carrol FI.Gray JL.Abraham P.Kuzemko MA.Lewin AH.Boja JW.Kuhar MJ. J. Med. Chem. 1993, 36: 2886 - 6
Diana GD.Volkots DL.Nitz TJ.Bailey TR.Long MA.Vescio N.Aldous S.Pevear DC.Dutko FJ. J. Med. Chem. 1994, 37: 2421 - 7
Ankersen M.Peschke B.Hansen BS.Hansen TK. Bioorg. Med. Chem. Lett. 1997, 7: 1293 - 8
Cheng C.Senanayake CH.Bill TJ.Larsen RD.Verhoeven TR.Reider PJ. J. Org. Chem. 1994, 59: 3738 -
9a
Buchanan JL.Vu CB.Ferry TJ.Corpuz EG.Pradeepan SG.Mani UN.Yang M.Plake HR.Varkhedkar VM.Lynch BA.MacNeil IA.Loiacono KA.Tiong CL.Holt DA. Bioorg. Med. Chem. Lett. 1999, 9: 2359 -
9b
Vu CB.Corpuz EG.Merry TJ.Pradeepan SG.Bartlett C.Bohacek RS.Botfield MC.Eyermann DJ.Lynch BA.MacNeil IA.Ram MK.van Schravendijk MR.Violette S.Sawyer TK. J. Med. Chem. 1999, 42: 4088 -
9c
Leite ACL.Vieira RF.de Faria AR.Wanderley AG.Afiatpour P.Ximenes ECPA.Srivastava RM.de Oliveira CF.Medeiros MV.Antunes E.Brondani DJ. Il Farmaco 2000, 55: 719 - 10
Rudolph J.Theis H.Hanke R.Endermann R.Johannsen L.Geschke F.-U. J. Med. Chem. 2001, 44: 619 - 11
Ohmoto K.Yamamoto T.Horiuchi T.Imanishi H.Odakagi Y.Kawabata K.Sekioka T.Hirota Y.Matsuoka S.Nakai H.Toda M. J. Med. Chem. 2000, 43: 4927 - 12
Rice KD.Nuss JM. Bioorg. Med. Chem. Lett. 2001, 11: 753 - 13
Sams CK.Lau J. Tetrahedron Lett. 1999, 40: 9359 -
14a
Borg S.Estenne-Bouhtou G.Luthman K.Csöregh I.Hesselink W.Hacksell U. J. Org. Chem. 1995, 60: 3112 -
14b
Borg S.Vollinga RC.Labarre M.Payza K.Terenius L.Luthman K. J. Med. Chem. 1999, 42: 4331 -
14c
Liang G.-B.Qian X. Bioorg. Med. Chem. Lett. 1999, 9: 2101 - 15
Bedford CD.Howd RA.Dailey OD.Miller A.Nolen HW.Kenley RA.Kern JR.Winterle JS. J. Med. Chem. 1986, 29: 2174 -
16a
Liang G.-B.Feng DD. Tetrahedron Lett. 1996, 37: 6627 -
16b
Deegan TL.Nitz TJ.Cebzanov D.Porco JA. Bioorg. Med. Chem. Lett. 1999, 9: 209 - 17
Young JR.DeVita RJ. Tetrahedron Lett. 1998, 39: 3931 - 18
De Melo SJ.Sobral AD.de Lima Lopes H.Srivastava RM. J. Braz. Chem. Soc. 1998, 9: 465 - 19
Hébert N.Hannah AL.Sutton SC. Tetrahedron Lett. 1999, 40: 8547 - 20
Poulain RF.Tartar AL.Déprez BP. Tetrahedron Lett. 2001, 42: 1495 -
21a
Kaboudin B.Navace K. Heterocycles 2003, 60: 2287 -
21b
Srivastava RM.Seabra GM. J. Braz. Chem. Soc. 1997, 8: 397 -
21c
Oussaid B.Moeini L.Martin B.Villemin D.Garrigues B. Synth. Commun. 1995, 25: 1451 -
22a
Hamzé A.Hernandez J.-F.Martinez J. Tetrahedron Lett. 2003, 44: 6079 -
22b
Hamzé A.Hernandez J.-F.Fulcrand P.Martinez J. J. Org. Chem. 2003, 68: 7316 -
23a
Braga AL.Appelt HR.Schneider PH.Silveira CC.Wessjohann LA. Tetrahedron: Asymmetry 1999, 10: 1733 -
23b
Braga AL.Appelt HR.Schneider PH.Rodrigues OED.Silveira CC.Wessjohann LA. Tetrahedron 2001, 57: 3291 -
23c
Braga AL.Appelt HR.Rodrigues OED.Silveira CC.Wessjohann LA.Schneider PH. Tetrahedron 2002, 58: 10413 -
23d
Braga AL.Vargas F.Andrade LH.Silveira CC. Tetrahedron Lett. 2002, 43: 2335 -
23e
Braga AL.Rodrigues OED.Paixão MW.Appelt HR.Silveira CC.Bottega DP. Synthesis 2002, 2338 -
23f
Braga AL.Silva SJN.Lüdtke DS.Drekener RL.Silveira CC.Rocha JBT.Wessjohann LA. Tetrahedron Lett. 2002, 43: 7329 -
23g
Braga AL.Paixão MW.Lüdtke DS.Silveira CC.Rodrigues OED. Org. Lett. 2003, 5: 2635 -
23h
Braga AL.Rubim RM.Schrekker HS.Wessjohann LA.de Bolster MWG.Zeni G.Sehnem JA. Tetrahedron: Asymmetry 2003, 14: 3291 - 24
Greene TW.Wuts PGM. In Protective Groups in Organic Synthesis 3rd ed.: John Wiley and Sons; New York: 1999. - 25
Eloy FRL. Chem. Rev. 1962, 62: 155 - 26
Still WC.Kahn M.Mitra A. J. Org. Chem. 1978, 43: 2923