The Synthesis of Novel Sulfamides and Cyclosulfamides Containing
Phosphonate Moiety
Nadia TRAD, Radia BOUASLA, Malika BERREDJEM* and Nour-Eddine AOUF
Laboratoire de Chimie Organique Appliquée (LCOA). Groupe de Chimie Bioorganique.
Faculté des Sciences. Université Badji Mokhtar. BP.12. 23000 Annaba-Algérie
E-mail : mberredjem@yahoo.fr
Phosphorus compounds containing the P-C bond are not particularly abundant in
nature. Their diverse biological activity, has for along time attracted considerable synthetic1
and pharmacological interest2. The Arbuzov reaction is regarded as the premier synthetic
method in the preparation of phosphonates, this reaction is very versatile way to form P-C
bond from the reaction of an phosphite and halide3.
In the course of our work on sulfamides 1 and cyclosulfamides4 derivatives 2 we have
prepared a number of phosphorus compounds 3, 4 and 5, for which, in a recent study,
biological activity properties as well as relationships between chemical structure/biological
activities were investigated.
In this report we describe in detail the preparation and reactivity of sulfamides and
cyclosulfamides containing phosphonate moiety starting from sulfonyl chloride and
chloroethyl amine in mild conditions, then cyclisation with K2CO3. The obtained compounds
1 and 2 were treated by triethylphophite to give phosphorylated compounds 3, 4 and 5.
NH2.HCl
Cl
H
N
SO2Cl2
NEt3
Cl
1
N
S
P
O
OEt
S
O
EtO
5
Cl
K2CO3
O
K2CO3
P
O
EtO
P
OEt
N
S
O
P(OEt)3
N
Cl
HN
O
O
O
H
N
H
N
O
2
P(OEt)3
O
O
H
N
S
O
P
P
O
OEt
4
OEt
HN
N
OEt
S
O
OEt
O
3
The structures of all compounds and intermediates reported herein were unambiguously
confirmed by usual spectroscopic methods: 1H, 31P and 13C NMR, MS and IR spectra.
References
1. (a) H-R. Hudson, L Powroznyk, M. Arbuzov, Arkivoc 2004, IX 19, (b) G.Syam,
M.Manjunath, K-R. Kumar, O-V. Reddy, C.Sures. Arkivoc 2006 XVI 128.
2. Monteil, M.; Guenin, E.; Migianu, E.; Lutomski, D and Lecouvey, M. Tetrahedron 61,
2005, 7528.
3. Bhattachary, A. K.; Thyarajan, G. Chem. Rev. 1981, 81, 415.
4. Malika Berredjem, Houria Djebbar , Zine Régainia, Nour-Eddine Aouf, Georges Dewynter
and Jean-Louis Montero. Phosphorus, Sulfur and Silicon 2003, 178, 693-705.