Abstract
Nitration of aromatic aminosulfonic acid primary amides to furnish the corresponding
sulfononitroamides has been described for the first time. The conditions of nitration
applied ensure chemoselective mononitration and prevent decomposition of the product.
Synthesis of dabsyl nitroamide sodium salt, as a potential β-amyloid aggregation inhibitor
is also reported.
Key words
sulfonamides - nitration - amines - arenes - azo compounds
References
<A NAME="RP02407SS-1A">1a</A>
Uehling DE.
Donaldson KH.
Deaton DN.
Hyman CE.
Sugg EE.
Barrett DG.
Hughes RG.
Reitter B.
Adkison KK.
Lancaster ME.
Lee F.
Hart R.
Paulik MA.
Sherman BW.
True T.
Cowan C.
J. Med. Chem.
2002,
45:
567
<A NAME="RP02407SS-1B">1b</A>
Lin SJ.
Shiao YJ.
Chi CW.
Yang LM.
Bioorg. Med. Chem. Lett.
2004,
14:
1173
<A NAME="RP02407SS-1C">1c</A>
Bubert Ch.
Blacker J.
Brown SM.
Crosby J.
Fitzjohn S.
Muxworthy JP.
Thorpe T.
Williams JMJ.
Tetrahedron Lett.
2001,
42:
4037
<A NAME="RP02407SS-1D">1d</A>
Caddick S.
Wilden JD.
Judd DB.
J. Am. Chem. Soc.
2004,
126:
1024
<A NAME="RP02407SS-2">2</A>
Crossley ML.
Northey EH.
Hultquist ME.
J. Am. Chem. Soc.
1939,
61:
2950
<A NAME="RP02407SS-3">3</A>
Murayama K.
Kinoshita T.
J. Chromatogr.
1981,
203:
349
<A NAME="RP02407SS-4">4</A>
Winnek PS.
Anderson GW.
Marson HW.
Faith HE.
Roblin OR.
J. Am. Chem. Soc.
1942,
64:
1682
<A NAME="RP02407SS-5">5</A>
Crossley ML.
Northey EH.
Hultquist ME.
J. Am. Chem. Soc.
1938,
60:
2222
<A NAME="RP02407SS-6">6</A>
Masereel B.
Lebrun P.
Dogné JM.
de Tullio P.
Pirotte B.
Pochet L.
Diouf O.
Delarge J.
Tetrahedron Lett.
1996,
37:
7253
<A NAME="RP02407SS-7A">7a</A>
Supuran CT.
Scozzafava A.
Briganti F.
Clare BW.
J. Med. Chem.
2000,
43:
1793
<A NAME="RP02407SS-7B">7b</A>
Rahman MK.
Aiba G.
Susan MABH.
Sasaya Y.
Ota K.
Watanabe M.
Macromolecules
2004,
37:
5572
<A NAME="RP02407SS-8A">8a</A>
Hinsberg O.
Ber. Dtsch. Chem. Ges.
1892,
25:
1092
<A NAME="RP02407SS-8B">8b</A>
Mathews BR.
J. Phys. Chem.
1920,
24:
108
<A NAME="RP02407SS-9">9</A>
Drozdova OA.
Astrat’ev AA.
Kuznetsov LL.
Selivanov VF.
Zh. Org. Khim.
1982,
18:
2335 ; Chem. Abstr. 1983, 98, 71312
<A NAME="RP02407SS-10">10</A>
Kozlova IK.
Luk’yanov OA.
Tartakowskii VA.
Izv. Akad. Nauk, Ser. Khim.
1981,
2556 ; Chem. Abstr. 1982, 96, 67902
<A NAME="RP02407SS-11">11</A>
Khromov-Borisov NW.
Zh. Prikl. Khim.
1945,
18:
612 ; Chem. Abstr. 1946, 40, 6365
<A NAME="RP02407SS-12">12</A>
Close WJ.
Sweet LR.
Brady LE.
Short JH.
Vernsten M.
J. Am. Chem. Soc.
1960,
82:
1132
<A NAME="RP02407SS-13">13</A>
Ilyushin MA.
Golod EL.
Gidaspov BV.
Zh. Org. Khim.
1977,
13:
11 ; Chem. Abstr. 1977, 86, 154698
<A NAME="RP02407SS-14">14</A>
Gallo-Rodriguez C.
Ji X.
Melman N.
Siegman BD.
Sanders LH.
Orlina J.
Fischer B.
Pu Q.
Olah ME.
van Galen PJM.
Stiles GL.
Jacobson KA.
J. Med. Chem.
1994,
37:
636
<A NAME="RP02407SS-15A">15a</A>
Drozdova OA.
Astrat’ev AA.
Kuznetsov LL.
Selivanov VF.
Zh. Org. Khim.
1983,
19:
761 ; Chem. Abstr. 1983, 99, 70018
<A NAME="RP02407SS-15B">15b</A>
Luk’yanov OA.
Gorelik WP.
Reshetova OS.
Tartakowskii VA.
Izv. Akad. Nauk, Ser. Khim.
1994,
1261 ; Chem. Abstr. 1995, 122, 132665
<A NAME="RP02407SS-16">16</A>
In the modified procedure for the isolation of 2i, the reaction mixture after pouring onto ice was extracted with EtOAc (4 × 15 mL).
The combined extracts were dried (MgSO4) and evaporated. The residue was chromatographed (silica gel, a hexane-EtOAc gradient
solvent from 10:1 to 1:1) to give 2i followed by recovered 1i. Analytical data of the product 2i (mp, R
f
, 1H and 13C NMR) were consistent with a commercial sample of 2,6-dichloro-4-nitroaniline.
<A NAME="RP02407SS-17">17</A>
Bell PH.
Roblin OR.
J. Am. Chem. Soc.
1942,
64:
2905
<A NAME="RP02407SS-18">18</A>
Schmidt O.
Ber. Dtsch. Ges. Chem.
1905,
38:
3201
<A NAME="RP02407SS-19">19</A>
Luk’yanov OA.
Onishchenko AA.
Salamonov YuB.
Ternikova TV.
Izv. Akad. Nauk., Ser. Khim.
1984,
1349 ; Chem. Abstr. 1985, 102, 5826
<A NAME="RP02407SS-20">20</A>
Kaupp G.
Herrmann A.
Schmeyers J.
Chem. Eur. J.
2002,
8:
1395
<A NAME="RP02407SS-21">21</A>
Blank B.
Farina FA.
Kerwin JF.
Saunders H.
J. Org. Chem.
1961,
26:
1551
<A NAME="RP02407SS-22">22</A>
Petrov V.
Stephenson O.
Wild AM.
J. Pharm. Pharmacol.
1960,
12:
705 ; Chem. Abstr. 1961, 55, 8336
<A NAME="RP02407SS-23">23</A>
Karman R.
Blaskó A.
Almarsson Ö.
Arasasingham R.
Bruice TC.
J. Am. Chem. Soc.
1992,
114:
4889
<A NAME="RP02407SS-24">24</A>
Vogel AI.
Vogel’s Textbook of Practical Organic Chemistry
5th ed.:
Longman;
London:
1989.
p.951
