Abstract
A series of convenient synthetic procedures are reported for pyrazole derivatives
with carbonyl or ester groups in the 3- and 5-positions and variable substitution
pattern at C4 and at the functional side arms. All compounds have been characterized
by 1 H and 13 C NMR spectroscopy, elemental analyses, and mass spectrometry. In addition, the structures
of several pyrazole derivatives have been determined by single crystal X-ray diffraction,
which provides insight into the effect of functional side arms on the hydrogen-bonded
supramolecular motifs of NH-pyrazoles.
Key words
pyrazoles - N-heterocycles - X-ray crystal structure - H-bonding
References
<A NAME="RZ26107SS-1">1 </A>
Dvorak CA.
Rudolph DA.
Ma S.
Carruthers NI.
J. Org. Chem.
2005,
70:
4188
2a </A>
Trofimenko S.
Prog. Inorg. Chem.
1986,
34:
115
2b </A>
La Monica G.
Ardizzoia GA.
Prog. Inorg. Chem.
1997,
46:
151
3 </A>
Klingele, J.; Dechert, S.; Meyer, F. Coord. Chem. Rev. , manuscript in preparation.
<A NAME="RZ26107SS-4">4 </A>
Rzepecki P.
Geib N.
Pfeifer M.
Biesemeier F.
Schrader T.
J. Org. Chem.
2007,
72:
3614
<A NAME="RZ26107SS-5">5 </A>
Noël G.
Röder JC.
Dechert S.
Pritzkow H.
Bolk L.
Mecking S.
Meyer F.
Adv. Synth. Catal.
2006,
348:
887
6a </A>
Aggarwal VK.
de Vicente J.
Bonnert RV.
J. Org. Chem.
2003,
68:
5381
6b </A>
Bishop BC.
Brands KMJ.
Gibb AD.
Kennedy DJ.
Synthesis
2004,
43
6c </A>
Padwa A.
1,3-Dipolar Cycloaddition Chemistry
Vol 1:
Wiley;
New York:
1984.
6d </A>
Stanovnik B.
Svete J.
In Science of Synthesis
Vol. 12:
Neier R.
Thieme;
Stuttgart:
2002.
p.15-225
<A NAME="RZ26107SS-7">7 </A>
Röder JC.
Meyer F.
Konrad M.
Sandhöfner S.
Kaifer E.
Pritzkow H.
Eur. J. Org. Chem.
2001,
4479
<A NAME="RZ26107SS-8">8 </A>
Cacchi S.
Fabrizi G.
Carangio A.
Synlett
1997,
959
<A NAME="RZ26107SS-9">9 </A>
Arán VJ.
Kumar M.
Molina J.
Lamarque L.
Navarro P.
Garcia-España E.
Ramirez JA.
Luis SV.
Escuder B.
J. Org. Chem.
1999,
64:
6135
<A NAME="RZ26107SS-10">10 </A>
Acerete C.
Bueno JM.
Campayo L.
Navarro P.
Rodríguez-Franco MI.
Samat A.
Tetrahedron
1994,
50:
4765
<A NAME="RZ26107SS-11">11 </A>
Schenck T.
Milne C.
Sawyer J.
Bosnich B.
Inorg. Chem.
1985,
24:
2334
<A NAME="RZ26107SS-12">12 </A>
Foces-Foces C.
Alkorta I.
Elguero J.
Acta Crystallogr., Sect. B
2000,
56:
1018
<A NAME="RZ26107SS-13">13 </A>
Jung ME.
Min S.-J.
Houk KN.
Ess D.
J. Org. Chem.
2004,
69:
9085
<A NAME="RZ26107SS-14">14 </A>
Rodríguez-Franco MI.
Dorronsoro I.
Hernández-Higueras AI.
Antequera G.
Tetrahedron Lett.
2001,
42:
863
<A NAME="RZ26107SS-15">15 </A>
Wolff L.
Justus Liebigs Ann. Chem.
1902,
325:
186
<A NAME="RZ26107SS-16">16 </A>
Buchner E.
v. Heide C.
Ber. Dtsch. Chem. Ges.
1902,
35:
<A NAME="RZ26107SS-17">17 </A>
Claramunt RM.
Cornago P.
Torres V.
Pinilla E.
Torres MR.
Samat A.
Lokshin V.
Valés M.
Elguero J.
J. Org. Chem.
2006,
71:
6881
<A NAME="RZ26107SS-18">18 </A>
Minkin VI.
Garnovskii AD.
Adv. Heterocycl. Chem.
2000,
76:
157
<A NAME="RZ26107SS-19">19 </A>
Fayos J.
Infantes L.
Cano FH.
Cryst. Growth Des.
2005,
1:
191
<A NAME="RZ26107SS-20">20 </A>
Infantes L.
Motherwell S.
Struct. Chem.
2004,
3:
173
<A NAME="RZ26107SS-21">21 </A>
Myhre PC.
Maxey CT.
Bebout DC.
Swedberg SH.
Petersen BL.
J. Org. Chem.
1990,
55:
3417
<A NAME="RZ26107SS-22">22 </A>
Meth-Cohn O.
Vuorinen E.
Modro TA.
J. Org. Chem.
1989,
54:
4822
23a </A>
Sheldrick GM.
SHELXL-97, Program for Crystal Structure Refinement
University of Göttingen;
Göttingen:
1997.
23b </A>
Sheldrick GM.
SHELXS-97, Program for Crystal Structure Solution
University of Göttingen;
Göttingen:
1997.
23c </A>
X-AREA
STOE & CIE GmbH;
Darmstadt:
2002.
23d </A>
X-RED
STOE & CIE GmbH;
Darmstadt:
2002.
24 </A>
CCDC-664760 (2 ), CCDC-664761 (5 ), CCDC-664762 (6 ), and CCDC-664763 (8 ) contain the supplementary crystallographic data for this paper. These data can be
obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge
Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033;
E-mail: deposit@ccdc.cam.ac.uk].
