Abstract
The bis-addition of arylhydrazines to α,β-unsaturated N -acylbenzotriazoles to form heterocyclic
compounds was achieved in refluxing THF by using triethylamine as
promoter. The reaction was highly regioselective and various 2-aryl-substituted
pyrazolidin-3-ones were obtained in moderate to good yields.
Key words
bis-addition - regioselectivity - arylhydrazine - α,β-unsaturated N -acylbenzotriazole - pyrazolidinone
References
1a Chen W.
Yuan XH.
Li R.
Du W.
Wu Y.
Ding
LS.
Chen YC.
Adv. Synth. Catal.
2006,
348:
1818
1b Pezdirc L.
Groselj U.
Meden A.
Stanovnik B.
Svete J.
Tetrahedron
Lett.
2007,
48:
5205 ;
and references cited therein
1c Couloigner E.
Cartier D.
Labia R.
Bioorg. Med.
Chem. Lett.
1999,
9:
2205
1d Blanchard WB, Britton TC, and Varie DL. inventors; US Patent 5399708.
; Chem. Abstr. 1995, 123, 228177
1e Holmes RE.
Neel DA.
Tetrahedron
Lett.
1990,
31:
5567
1f Jungheim LN.
Sigmund SK.
J.
Org. Chem.
1987,
52:
4007
1g Indelicato JM.
Pasini CE.
J.
Med. Chem.
1988,
31:
1227
1h Long WE, Tirel MD, Gent MH, and Webb
TC. inventors; US
Patent 4753869.
; Chem. Abstr. 1988 , 105, 143486
1i Ernest FG. inventors; US Patent 3178441.
; Chem. Abstr. 1965 , 63,
39145
2a Perri ST.
Slater SG.
Toske SG.
White JD.
J. Org. Chem.
1990,
55:
6037
2b Shi H.
Zhu HJ.
Wang JT.
Acta
Crystallogr., Sect. E: Struct. Rep. Online
2006,
62:
233
2c Shi H.
Zhu HJ.
Yin PW.
Wang JT.
Shi
XL.
Acta Crystallogr., Sect. E: Struct. Rep. Online
2005,
61:
2246
2d Marton GL.
Marton AL.
Rev.
Chim. (Bucharest, Rom.)
2004,
55:
555 ; Chem. Abstr. 2004 , 142, 197957
2e Marton AL.
Marton GI.
Rev.
Chim. (Bucharest, Rom.)
2002,
53:
51 ; Chem. Abstr. 2002 , 137, 125117
2f Taniguchi M, and Yamakawa K. inventors; Japanese Patent 11060559.
; Chem. Abstr. 1997 , 130,
223270
3 Sibi MP.
Soeta T.
J. Am. Chem. Soc.
2007,
129:
4522
4 Kim KS.
Ryan PC.
Heterocycles
1990,
31:
79
5 Katritzky AR.
Suzuki K.
Wang Z.
Synlett
2005,
1656
6 Katritzky AR.
Wang M.
Zhang S.
Arkivoc
2001,
(ix):
19
7 Katritzky AR.
Cai C.
Singh SK.
J.
Org. Chem.
2006,
71:
3375
8 Wang XX.
Zou XF.
Du JX.
J.
Chem. Res., Synop.
2006,
64
9 Katritzky AR.
Meher NK.
Singh SK.
J.
Org. Chem.
2005,
70:
7792
10 Katritzky AR.
Le KNB.
Khelashvili L.
Mohapatra PP.
J.
Org. Chem.
2006,
71:
9861
11 Zou XF.
Wang XX.
Cheng CG.
Kong LC.
Mao H.
Tetrahedron
Lett.
2006,
47:
3767
12 Wang XX.
Yu HP.
Xu PF.
Zheng RW.
J. Chem. Res., Synop.
2005,
595
13a Diab J.
Laurent A.
Drean IL.
J. Fluorine Chem.
1997,
84:
145
13b Touzot A.
Soufyane M.
Berber H.
Toupet L.
Mirand C.
J.
Fluorine Chem.
2004,
125:
1299
14 Crystal data for 4aa :
C16 H16 N2 O2 , Mr = 268.31,
colorless crystal (0.41 × 0.15 × 0.05
mm), monoclinic, space group P 21 /c , a = 8.6609(4) Å, b = 6.0272(3) Å, c = 27.1719(13) Å, β = 105.494(4)˚, V = 1366.85(11) ų , Z = 4, T = 296(2)
K, ρcalcd = 1.304
g˙cm-³ , F (000) = 568, µ = 0.087
mm-¹ , R 1 = 0.0594, wR 2 = 0.1527
and S = 1.048
for 1810 reflections with I > 2σ(I ).
The structure was solved by direction methods and difference Fourier
syntheses. Nonhydrogen atoms were refined anisotropically, and all hydrogen
atoms were placed at ideal positions and allowed to ride. The crystallographic
calculations were conducted using the SHELXL-97 programs. Detail
crystallographic data of 4aa have been
deposited at Cambridge Crystallographic Data Center under CCDC-687432.
These data can be obtained free of charge from 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 336 033; e-mail: deposit@ccdc.cam.ac.uk.
15a Bishiop BC.
Brands KMJ.
Gibb AD.
Kennedy DJ.
Synthesis
2004,
43
15b Xie F.
Cheng G.
Hu YH.
J. Comb.
Chem.
2006,
8:
286
16 Katritzky AR.
Zhang Y.
Singh SK.
Synthesis
2003,
2795
