RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2007(9): 1355-1358
DOI: 10.1055/s-2007-965994
DOI: 10.1055/s-2007-965994
PAPER
© Georg Thieme Verlag Stuttgart · New York
Efficient Synthesis of Sulfonimidoylguanidines by Coupling of Sulfonimidamides with Uronium Reagents
Weitere Informationen
Received
22 February 2007
Publikationsdatum:
23. März 2007 (online)
Publikationsverlauf
Publikationsdatum:
23. März 2007 (online)
Abstract
Novel guanidine derivatives can be prepared in good to excellent yields by coupling of sulfonimidamides with uronium reagents under basic conditions.
Key words
guanidine - sulfonimidamide - uronium reagent - guanylation
-
1a
Costa M.Chiusoli GP.Taffurelli D.Dalmanego G. J. Chem. Soc., Perkin Trans. 1 1998, 1541 -
1b
Kovacecic B.Maksic ZB. Org. Lett. 2001, 3: 1523 - 2
Yamamoto Y.Kojima S. In The Chemistry of Amidines and Imidates Vol. 2:Patai S.Rappoport Z. Wiley; New York: 1991. p.485 -
3a
Berlinck RGS. Fortschr. Chem. Org. Naturst. 1995, 66: 119 -
3b
Berlinck RGS. Nat. Prod. Rep. 1996, 13: 377 -
3c
Berlinck RGS. Nat. Prod. Rep. 1999, 16: 339 -
3d
Berlinck RGS. Nat. Prod. Rep. 2002, 19: 617 -
3e
Berlinck RGS. Nat. Prod. Rep. 2005, 22: 516 - 4
Berlinck RGS.Kossuga MH.Nascimento AM. In Science of Synthesis Vol. 8:Knight JG. Thieme; Stuttgart: 2005. p.1077 - 5
Gluszok S.Goossens L.Depreux P.Hénichart J.-P. Tetrahedron Lett. 2006, 47: 6087 - For the synthesis of N-(p-toluenesulfonyl)-p-toluenesulfon-imidamide (1a), see:
-
6a
Di Chenna PH.Robert-Peillard F.Dauban P.Dodd RH. J. Org. Chem. 2004, 6: 4503 -
6b
Fruit C.Robert-Peillard F.Bernardinelli G.Müller P.Dodd RH.Dauban P. Tetrahedron: Asymmetry 2005, 16: 3481 - For the synthesis and application of N-benzoyl-p-toluene-sulfonimidamide (1b), see:
-
7a
Leca D.Toussaint A.Mareau C.Fensterbank L.Lacôte E.Malacria M. Org. Lett. 2004, 6: 3573 - For the intermediate steps, see:
-
7b
Mintz MJ.Walling C. Org. Synth. 1969, 49: 9 -
7c
Backes BJ.Drogli DR.Ellman JA. J. Org. Chem. 1999, 64: 5472 -
7d
Krasnova LB.Yudin AK. J. Org. Chem. 2004, 69: 2584 -
7e
Saville CK.Magloire VP.Kazlauskas RJ. J. Am. Chem. Soc. 2005, 127: 2104