Abstract
A functionalisation of 1,3-diones using hypervalent iodine has been developed that is useful in the preparation of libraries of heterocyclic compounds.
Key words
iodosylbenzene - alcohols - combinatorial chemistry - heterocycles - diones
References
1 Hobbs De Witt S. In
The Practice of Medicinal Chemistry
Wermuth CG.
Academic Press;
San Diego:
2001.
2 Deegan TL.
Nitz TJ.
Cebzanov D.
Pufko DE.
Porco JA.
Bioorg. Med. Chem. Lett.
1999,
9:
209
3 Joule JA.
Mills K.
Heterocyclic Chemistry
Blackwell Science;
Oxford:
2000.
4 Koser GF.
Aldrichimica Acta
2001,
34:
89
5 Moriarty RM.
Kosmeder JW. In
Encyclopedia of Reagents for Organic Synthesis
Vol. 5:
Paquette LA.
John Wiley and Sons;
Chichester:
1995.
6 Baum JS.
Shook DA.
Davies HML.
Smith HD.
Synth. Commun.
1987,
17:
1709
7a Cox GC.
Miller DJ.
Moody CJ.
Sie EH.
Kulagowski JJ.
Tetrahedron
1994,
50:
3195
7b Kettle JG.
Faull AW.
Fillery SM.
Flynn AP.
Hoyle MA.
Hudson JA.
Tetrahedron Lett.
2000,
41:
6905
7c Nelson TD.
Song JK.
Thompson AS.
Zhao M.
DeMarco A.
Reamer RA.
Huntington MF.
Grabowski EJJ.
Reider PJ.
Tetrahedron Lett.
2000,
41:
1877
8 Moriarty RM.
Vaid RK.
Ravikumar VT.
Vaid BK.
Hopkins TE.
Tetrahedron
1988,
44:
1603
9a Ochiai M.
Sumi K.
Takaoka Y.
Kunishima M.
Nagao Y.
Shiro M.
Fujita E.
Tetrahedron
1988,
44:
4095
9b Ochiai M.
Kunishima M.
Sumi K.
Nagao Y.
Tetrahedron Lett.
1985,
26:
4501
9c Ochiai M.
Ito T.
Takaoka Y.
Masaki Y.
Kunishima M.
Tani S.
Nagao Y.
J. Chem. Soc., Chem. Commun.
1990,
118
10a Ochiai M.
Takaoka Y.
Nagao Y.
J. Am. Chem. Soc.
1988,
110:
6565
10b Ochiai M.
Kunishima M.
Tani S.
Nagao Y.
J. Am. Chem. Soc.
1991,
113:
3135
10c Ochiai M.
Uemara K.
Masaki Y.
J. Am. Chem. Soc.
1993,
115:
2528
11 The reactions were conducted in 96 well plates and the experimental procedure for a representative sample was as follows: To a solution of 3-methylbenzyl alcohol (14 mg, 117 µmol) in chloroform (0.25 mL) was added 3,5-heptanedione (10 mg, 78 µmol) in chloroform (0.20 mL), boron trifluoride etherate (12 µl, 93µmol) and iodosyl-benzene (20 mg, 93 µmol). After being shaken for 12 h water (0.30 mL) was added and the plate shaken for a further8 column eluted with trifluoroacetic acid in water(0.1% v/v): acetonitrile (95:5) (10 mL/min) to furnish 3,5-diethyl-1H -pyrazol-4-yl-3-methylbenzyl ether (5 mg, 28%); retention time 3.24 min; 1 H NMR (500 MHz; CDCl3 ): δ = 7.26 (1 H, dd, J = 7.4, 7.4 Hz), 7.20 (1 H, s), 7.17 (1 H, d, J = 7.4 Hz), 7.15 (1 H, d, J = 7.4 Hz), 4.78 (2 H, s), 2.53 (4 H, q, J = 7.7 Hz), 2.37 (3 H, s), 1.21 (6 H, t, J = 7.7 Hz); LRMS: m/z = 245, MH+ .
12 Moriarty RM.
Vaid RK.
Duncan MP.
Ochiai M.
Inenaga I.
Nagao Y.
Tetrahedron Lett.
1988,
29:
6913
