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 2003(6): 0845-0848
DOI: 10.1055/s-2003-38684
DOI: 10.1055/s-2003-38684
PAPER
© Georg Thieme Verlag Stuttgart ˙ New YorkSynthesis of N-Tosylguanidines by Ring Cleavage of 1,2-Dihydro-2-tosyliminopyrimidines
Further Information
Received
6 February 2003
Publication Date:
16 April 2003 (online)
Publication History
Publication Date:
16 April 2003 (online)

Abstract
The present communication discloses a new synthetic method for the preparation of N-tosylguanidines in high yields by ring cleavage of 1,2-dihydro-2-tosyliminopyrimidines with methylamine.
Key words
imines - ring opening - nucleophilic addition - sulfonamides - cleavage
- 1a
Rabinowitz MH.Andrews RC.Becherer JD.Bickett DM.Bubacz DC.Conway JG.Cowan DJ.Gaul M.Glennon K. J. Med. Chem. 2001, 44: 4252 - 1b
Scozzafava A.Nicolae A.Maior O.Briganti F.Supuran CT. J. Enzyme Inhib. 1998, 14: 49 - 1c
Berlinck RGS. Nat. Prod. Rep. 1996, 13: 377 - 1d
Laxma Reddy N.Hu L.-Y.Cotter RE.Fischer JB.Wong WJ.McBurney RN.Weber E.Holmes DL.Wong ST.Prasad R.Keana JFW. J. Med. Chem. 1994, 37: 260 - 2a
Supuran TC.Scozzafava A.Briganti F.Clare BW. J. Med. Chem. 2000, 43: 1793 - 2b
Greenhill JL.Lue P. In Progress in Medicinal Chemistry Vol. 30, Chap. 5:Ellis GP.Luscombe DK. Elsevier; Amsterdam: 1993. - 2c
Burell G.Evans JM.Hicks F.Stemp G. Bioorg. Med. Chem. Lett. 1993, 3: 999 - 3a
Zhang J.Shi Y. Tetrahedron Lett. 2000, 41: 8075 - 3b
Feichtinger K.Zapf C.Sings HL.Goodman M. J. Org. Chem. 1998, 63: 3804 - 3c
Schlama T.Gouverneur V.Valleix A.Greiner A.Toupet L.Mioskowski C. J. Org. Chem. 1997, 62: 4200 - 3d
Zhong HM.Greco MN.Maryanoff BR. J. Org. Chem. 1997, 62: 9326 - 3e
Yong YF.Kowalski JA.Lipton MA. J. Org. Chem. 1997, 62: 1540 - 3f
Barvian MR.Showalter HDH.Doherty AM. Tetrahedron Lett. 1997, 38: 6799 - 3g
Levallet C.Lerpiniere J.Ko SY. Tetrahedron 1997, 53: 5291 - 3h
Bossio R.Marcaccini S.Pepino R. Tetrahedron Lett. 1995, 36: 2325 - 3i
Ramadas K.Srinivasan N. Tetrahedron Lett. 1995, 36: 2841 - 3j
Lemcke T.Mesinger P. Archiv. Pharm. (Weinheim, Ger.) 1995, 328: 269 - 3k
Kutepov DF.Khokhlov DN.Tuzhilina VL. Zh. Obshch. Khim. 1961, 31: 2825 ; Chem. Abstr. 1962, 56, 14027 - 4
Acero-Alarcón A.Armero-Alarte T.Jordá-Gregori JM.Rojas-Argudo C.Zaballos-García E.Server-Carrió J.Ahjyaje FZ.Sepulveda-Arques J. Synthesis 1999, 2124 - 6
Hamdouchi C.Blas J.Prado M.Gruber J.Heinz BA.Vance L. J. Med. Chem. 1999, 42: 50 - 7a
El Ashry ESH.El Kilany N.Rashed N.Assafir H. Adv. Heterocl. Chem. 2000, 75: 79 - 7b
Biffin MEC.Brown DJ. Tetrahedron Lett. 1967, 2029 - 7c
Hayes DH.Hayes-Baron F. J. Chem. Soc. (C) 1967, 1528 - 7d
Biffin MEC.Brown DJ.Porter QN. J. Chem. Soc., (C) 1968, 2159 - 7e
Van der Plas HC.Jonjegan H. Tetrahedron Lett. 1967, 4385 - 8
Brown DJ.Ford PW.Paddon-Row MN. J. Chem. Soc., C 1968, 1452
References
Fernandez-Ferri, P.; Ubeda, A.; Guillén, I.; Lasri, J.; González-Rosende, M. E.; Akssira, M.; Sepúlveda-Arques, J. Eur. J. Med. Chem. 2003, in press.