Abstract
Perhydropyrimidin-2-ylium and perhydro-1,3-diazepin-2-ylium iodides with linked 1,3-oxathiolane
ring were obtained. These new, water-soluble derivatives of 1,3-oxathiolane were prepared
by cyclocondensation of diiodomethane with appropriate zwitterionic derivatives of
2-hydroxypropionic acid. The iodides were exploited in metathesis process with various
anions.
Key words
zwitterionic compounds - saturated heterocycles - 1,3-oxathiolane - antimicrobial
activity
References
<A NAME="RZ07505SS-1">1 </A>
Kramer W,
Weissmueller J,
Reiser W,
Berg D,
Brandes W, and
Reinecke P. inventors; Ger Offen., DE 3420828.
; Chem . Abstr . 1986 , 104 , 64212
<A NAME="RZ07505SS-2">2 </A>
Angeli P.
Gianella M.
Pigini M.
Gualtieri F.
Teodori E.
Valsecchi B.
Givaraghi G.
Eur. J. Med. Chem.
1985,
20:
517
<A NAME="RZ07505SS-3">3 </A>
Yokoyama M,
Togo H,
Kubo M,
Baba K,
Yamamoto Y, and
Kudou M. inventors; Jpn. Kokai Tokkyo Koho, JP 1129567 (9929567).
; Chem . Abstr . 1999 , 130 , 193113
<A NAME="RZ07505SS-4">4 </A>
Belleau B,
Belleau P, and
Nguyen-Ba N. inventors; U.S. Patent, US 200120026.
; Chem . Abstr . 2001 , 135 , 211232
<A NAME="RZ07505SS-5">5 </A>
Mansour TS, and
Jin H. inventors; U.S. Patent, US 6228860.
; Chem . Abstr . 2001 , 134 , 336206
<A NAME="RZ07505SS-6">6 </A>
Carroll SS,
MacCoss M,
Kuo LC,
Olsen DB,
Bhat B,
Eldrup AB,
Prhavc M,
Malik L, and
Bera S. inventors; PCT Int. Appl., WO 0320222.
; Chem . Abstr . 2003 , 138 , 221789
<A NAME="RZ07505SS-7">7 </A>
Gumina G.
Song G.-Y.
Chu CK.
FEMS Microbiol. Lett.
2001,
202:
9
<A NAME="RZ07505SS-8">8 </A>
Mansour TS.
Evans CA.
Charron M.
Korba BE.
Bioorg. Med. Chem. Lett.
1997,
7:
303
<A NAME="RZ07505SS-9">9 </A>
Hirano H,
Nakamura Y,
Nagata H, and
Tamura H. inventors; Jpn. Kokai Tokkyo Koho, JP 2001316386.
; Chem . Abstr . 2001 , 135 , 357913
<A NAME="RZ07505SS-10">10 </A>
Hirano H,
Nakamura Y,
Nagata H, and
Tamura H. inventors; Jpn. Kokai Tokkyo Koho, JP 200139972.
; Chem . Abstr . 2001 , 134 , 146752
<A NAME="RZ07505SS-11">11 </A>
Djerassi C.
Gorman M.
J. Am. Chem. Soc.
1953,
75:
3704
<A NAME="RZ07505SS-12">12 </A>
Ralls JW.
Dodson RM.
Riegel B.
J. Am. Chem. Soc.
1949,
71:
3320
<A NAME="RZ07505SS-13">13 </A>
Wilson GE.
Huang MG.
Schloman WW.
J. Org. Chem.
1968,
33:
2133
<A NAME="RZ07505SS-14">14 </A>
Kamal A.
Chouhan G.
Ahmed K.
Tetrahedron Lett.
2002,
43:
6947
<A NAME="RZ07505SS-15">15 </A>
Karimi B.
Seradj H.
Synlett
2000,
805
<A NAME="RZ07505SS-16">16 </A>
Blagoev M.
Linden A.
Heimgartner H.
Helv. Chim. Acta
2000,
83:
3163
<A NAME="RZ07505SS-17">17 </A>
Fu C.
Linden A.
Heimgartner H.
Helv. Chim. Acta
2001,
84:
3319
<A NAME="RZ07505SS-18">18 </A>
Zaleska B.
Karelus M.
Synlett
2002,
1831
<A NAME="RZ07505SS-19">19 </A>
Zaleska B.
Bazanek T.
Socha R.
Karelus M.
Grochowski J.
Serda P.
J. Org. Chem.
2002,
67:
2203