5
4
5
6
.
.
.
Ding, R.; He, Y.; Xu, J.; Liu, H.; Wang, X.; Feng, M.; Qi, C.;
Zhang, J. Molecules. 2010, 15, 8723.
19. Saikia, P.; Kaishap, P. P.; Prakash, R.; Shekarrao, K.; Gogoi,
S.; Boruah, R. C. Tetrahedron Lett. 2014, 55, 3896.
20. Yin, L.; Liebscher, J. Synthesis. 2004, 2329.
Shaaban, M. R.; Saleh, T. S.; Mayhoub, A. S.; Mansour, A.;
Farag, A. M. Biorg. Med. Chem. 2008, 16, 6344.
2
1. Representative procedure for the synthesis of 5,7-
diarylpyrazolo[1,5-a]pyrimidine (3): An oven dried 25 mL RB
flask was charged with chalcone (1.0 mmol), 3-aminopyrazole
Auzzi, G.; Bruni, F.; Cecchi, L.; Costanzo, A.; Pecori Vettori, L.;
Pirisino, R.; Corrias, M.; Ignesti, G.; Banchelli, G.; Raimondi, L.
J. Med. Chem. 1983, 26, 1706.
(
1.2 mmol), KOH (0.1 mmol) and DMF (5 mL). The resulting
7
8
.
.
Senga, K.; Novinson, T.; Springer, R. H.; Rao, R. P.; O'Brien, D.
E.; Robins, R. K.; Wilson, H. R. J. Med. Chem. 1975, 18, 312.
Fraley, M. E.; Hoffman, W. F.; Rubino, R. S.; Hungate, R. W.;
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Kendall, R. L.; Coll, K. E.; Thomas, K. A. Biorg. Med. Chem.
Lett. 2002, 12, 2767.
solution was stirred at 110 °C for 20 min. On completion, the
reaction mass was allowed to cool to ambient temperature,
diluted with water (20 mL) and extracted into ethyl acetate (2 ×
2
0 mL). The combined organic layers were dried over anhydrous
Na SO , and organic solvent was evaporated on a rotatory
2
4
evaporator. The crude residue was purified by column
chromatography (silica gel 60-120 mesh, eluent 20%
EtOAc/hexanes).
9
.
(a) Wustrow, D. J.; Capiris, T.; Rubin, R.; Knobelsdorf, J. A.;
Akunne, H.; Davis, M. D.; MacKenzie, R.; Pugsley, T. A.;
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1
998, 8, 2067; (b) Gilligan, P. J.; Baldauf, C.; Cocuzza, A.;
Spectroscopic data for selected compounds:
Chidester, D.; Zaczek, R.; Fitzgerald, L. W.; McElroy, J.; Smith,
M. A.; Shen, H. S. L.; Saye, J. A.; Christ, D.; Trainor, G.;
Robertson, D. W.; Hartig, P. Biorg. Med. Chem. 2000, 8, 181.
5
,7-Diphenylpyrazolo[1,5-a]pyrimidine (3a): Yield 89%; Off-
20
white solid; mp 83−85 °C (Ref. 85-86 °C); (20% EtOAc in
1
hexane); H NMR (300 MHz, CDCl
.18 – 8.13 (m, 2H), 8.09 (dd, J = 6.5, 2.6 Hz, 2H), 7.64 – 7.58
m, 3H), 7.57 – 7.50 (m, 3H), 7.36 (s, 1H), 6.83 (d, J = 2.2 Hz,
3
) δ 8.20 (d, J = 2.2 Hz, 1H),
1
1
0. Compton, D. R.; Sheng, S.; Carlson, K. E.; Rebacz, N. A.; Lee, I.
Y.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med.
Chem. 2004, 47, 5872.
8
(
1
3
1
1
1
3
H); C NMR (126 MHz, CDCl ) δ 156.20, 149.89, 146.84,
1. Almansa, C.; de Arriba, A. F.; Cavalcanti, F. L.; Gómez, L. A.;
Miralles, A.; Merlos, M.; García-Rafanell, J.; Forn, J. J. Med.
Chem. 2001, 44, 350.
45.20, 137.54, 131.54, 130.96, 130.31, 129.27, 128.95, 128.73,
27.29, 105.20, 97.20.
1
1
2. Al-Sehemi, A. G.; Irfan, A.; Fouda, A. M. Spectrochim. Acta
Mol. Biomol. Spectros. 2013, 111, 223.
2-(4-Fluorophenyl)-5,7-diphenylpyrazolo[1,5-a]pyrimidine (3e):
Yield 82%; Ash colour solid; mp 157−158 °C; (10% EtOAc in
1
hexane); H NMR (400 MHz, CDCl
3. (a) Anwar, H. F.; Elnagdic, M. H. ARKIVOK. 2009, 198; (b)
Zeng, L.-Y.; Cai, C. J. Comb. Chem. 2009, 12, 35; (c) Xin, X.;
Wang, Y.; Xu, W.; Lin, Y.; Duan, H.; Dong, D. Green Chem.
3
) δ 8.26 – 8.21 (m, 2H),
8.19 – 8.17 (m, 1H), 8.17 – 8.15 (m, 1H), 8.06 – 7.99 (m, 2H),
7.66 – 7.61 (m, 3H), 7.59 – 7.51 (m, 3H), 7.39 (s, 1H), 7.20 –
1
3
2
010, 12, 893.
3
7.13 (m, 2H), 7.06 (s, 1H); C NMR (101 MHz, CDCl ) δ
1
1
4. (a) Goswami, S.; Jana, S.; Hazra, A.; Adak, A. K. J. Heterocycl.
Chem. 2007, 44, 1191; (b) Rao, V. K.; Tiwari, R.; Chhikara, B.
S.; Shirazi, A. N.; Parang, K.; Kumar, A. RSC Advances. 2013,
163.34 (d, J = 248.01 Hz), 156.24, 155.34, 151.19, 146.39,
137.57, 131.44, 131.04, 130.32, 129.52, 129.31 (d, J = 3.12 Hz),
128.97, 128.62, 128.39 (d, J = 8.26 Hz), 127.26, 115.68 (d, J =
21.65Hz), 105.13, 93.54.
3
, 15396.
5. (a) Hussein, A. M.; Ishak, E. A.; Atalla, A. A.; Hafiz, S. A.;
2
4
-(7-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)phenol (3p): Yield
1
1%; Yellow solid; mp 174−176 °C; (15% EtOAc in hexane); H
Elnagdi, M. H. Phosphorus, Sulfur Silicon Relat. Elem. 2007,
1
82, 2897; (b) Poreba, K.; Opolski, A.; Wietrzyk, J.; Kowalska,
NMR (300 MHz, CDCl
3
) δ 13.63 (s, 1H), 8.18 (d, J = 1.7 Hz,
H), 8.11 – 8.02 (m, 2H), 7.87 (d, J = 7.9 Hz, 1H), 7.62 (d, J =
.9 Hz, 3H), 7.45 – 7.35 (m, 2H), 7.10 (d, J = 8.2 Hz, 1H), 6.97
M. Arch. Pharm. 2001, 334, 219; (c) Elgemeie, G. E. H.; Fathy,
N. M.; Faddah, L. M.; Ebeid, M. Y.; Elsaid, M. K. Arch. Pharm.
1
2
1
991, 324, 149; (d) Quiroga, J.; Insuasty, B.; Rincon, R.;
Larrahondo, M.; Hanold, N.; Meier, H. J. Heterocycl. Chem.
994, 31, 1333; (e) Sayed, A. Z.; Aboul-Fetouh, M. S.; Nassar,
1
3
(
t, J = 7.4 Hz, 1H), 6.72 (d, J = 1.8 Hz, 1H); C NMR (75 MHz,
CDCl ) δ 160.64, 157.24, 147.87, 146.71, 145.37, 132.95,
31.30, 131.15, 129.34, 128.80, 127.34, 119.17, 118.86, 117.70,
03.48, 96.29.
3
1
1
1
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1
1
1
6. Lipson, V. V.; Desenko, S. M.; Borodina, V. V.; Shirobokova,
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1
854.
8. (a) Pericherla, K.; Jha, A.; Khungar, B.; Kumar, A. Org. Lett.
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2
1
Chem. Commun. 2013, 49, 2924; (d) Pericherla, K.; Khungar, B.;
Kumar, A. Tetrahedron Lett. 2012, 53, 1253; (e) Kaswan, P.;
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