Abstract
2-Heptyl-4(1H )-quinolone was converted in two steps into the 4-ethoxycarbonyloxy-, 4-(tert -butoxycarbonyloxy)-, and 4-(dimethylaminocarbonyloxy)quinoline N -oxides. While the former two rearranged to the corresponding 1-(alkoxycarbonyloxy)-4(1H )-quinolones at room temperature, the latter was stable, even at 140 °C in refluxing xylenes. Basic hydrolysis of these compounds furnished 2-heptyl-1-hydroxy-4(1H )-quinolone.
Key words
acylations - heterocycles - quinolines - rearrangements - oxidations
References
1 Lightbown JW.
Nature (London)
1950,
166:
356
2 Lightbown JW.
J. Gen. Microbiol.
1954,
11:
477
3 Cornforth JW.
James AT.
Biochem. J.
1956,
63:
124
4 Lightbown JW.
Jackson FL.
Biochem. J.
1956,
63:
130
5 Reil E.
Höfle G.
Draber W.
Oettmeier W.
Biochim. Biophys. Acta
1997,
1318:
291
6 von Jagow G.
Link TA.
Methods Enzymol.
1986,
126:
253
7 Reil E.
Höfle G.
Draber W.
Oettmeier W.
Biochim. Biophys. Acta
2001,
1506:
127
8a Pils D.
Gregor W.
Schmetterer G.
FEMS Microbiol. Lett.
1997,
152:
83
8b Pils D.
Schmetterer G.
FEMS Microbiol. Lett.
2001,
203:
217
9 Kunze B.
Höfle G.
Reichenbach H.
J. Antibiot.
1987,
40:
258
10a Oettmeier W.
Dostatni R.
Majewski C.
Höfle G.
Fecker T.
Kunze B.
Reichenbach H.
Z. Naturforsch., C: Biosci.
1990,
45:
322
10b Meunier B.
Madgwick SA.
Reil E.
Oettmeier W.
Rich PR.
Biochemistry
1995,
34:
1076
11 Wells IC.
J. Biol. Chem.
1952,
196:
331
12 Ames DE.
Franklin CS.
Grey TF.
J. Chem. Soc.
1956,
3079
13 Bradbury RH.
Allott CP.
Dennis M.
Fisher E.
Major JS.
Masek BB.
Oldham AA.
Pearce RJ.
Rankine N.
Revill JM.
Roberts DA.
Russell ST.
J. Med. Chem.
1992,
356:
4027
14 Miyoshi H.
Takegami K.
Sakamoto K.
Mogi T.
Iwamura H.
J. Biochem.
1999,
125:
138
15 Studeneer A, Salbeck G, Emmel L, and Kauf W. inventors; (Hoechst AG) Ger. Offen. DE 2432635.
; Chem. Abstr. 84, 150525y
16 Mikenda W.
Vib. Spectrosc.
1992,
3:
327
17 Bruker programs: SMART, version 5.629; SAINT, version 6.45; SADABS, version 2.10; SHELXTL, version 6.14 (Bruker AXS Inc.; Madison, WI, 2003 ).
18 Sheldrick GM.
SHELX97: Program System for Crystal Structure Determination
University of Göttingen;
Germany:
1997.
19 Epstein J.
Cannon P.
Swidler R.
Baraze A.
J. Org. Chem.
1977,
42:
759
20 Katzenellenbogen JA.
Utawanit T.
J. Am. Chem. Soc.
1974,
96:
6153
21 CCDC 616835-616836 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data.requecst/cif.
