Keywords
5-aminopyrazoles
chemoselectivity
heterocyclization
itaconimides
pyrazolo[3,4-b]pyridines
recyclization
Abstract
New polyfunctional hydrogenated pyrazolo[3,4-b]pyridines were obtained by the chemoselective reaction between N-arylitaconimides and 5-aminopyrazoles. The transformation is the cascade reaction including Michael addition at the active double bond of the itaconimide followed by the intramolecular transamidation and recyclization.
References
1.
Manetti F., Schenone S., Bondavalli F., Brullo C., Bruno O., Ranise A., Mosti L., Menozzi G., Fossa P., Trincavelli M.L., Martini C., Martinelli A., Tintori C., Botta M.
Journal of Medicinal Chemistry,
2005
2.
Falcó J.L., Lloveras M., Buira I., Teixidó J., Borrell J.I., Méndez E., Terencio J., Palomer A., Guglietta A.
European Journal of Medicinal Chemistry,
2005
3.
Witherington J., Bordas V., Garland S.L., Hickey D.M., Ife R.J., Liddle J., Saunders M., Smith D.G., Ward R.W.
Bioorganic and Medicinal Chemistry Letters,
2003
4.
K. Dodiya D., R. Trivedi A., B. Kataria V., H. Shah V.
Current Organic Chemistry,
2012
5.
Chavva K., Pillalamarri S., Banda V., Gautham S., Gaddamedi J., Yedla P., Kumar C.G., Banda N.
Bioorganic and Medicinal Chemistry Letters,
2013
6.
Ghaedi A., Bardajee G.R., Mirshokrayi A., Mahdavi M., Shafiee A., Akbarzadeh T.
RSC Advances,
2015
7.
Hamblin J.N., Angell T.D., Ballantine S.P., Cook C.M., Cooper A.W., Dawson J., Delves C.J., Jones P.S., Lindvall M., Lucas F.S., Mitchell C.J., Neu M.Y., Ranshaw L.E., Solanke Y.E., Somers D.O., et. al.
Bioorganic and Medicinal Chemistry Letters,
2008
8.
10.1016/j.mencom.2022.09.041_b0035
Tucker
Patent W0 2009117278 A2,
2009
9.
Sharma P.K., Singh K., Kumar S., Kumar P., Dhawan S.N., Lal S., Ulbrich H., Dannhardt G.
Medicinal Chemistry Research,
2010
10.
Meyers J., Carter M., Mok N.Y., Brown N.
Future Medicinal Chemistry,
2016
11.
Lovering F., Bikker J., Humblet C.
Journal of Medicinal Chemistry,
2009
12.
Morley A.D., Pugliese A., Birchall K., Bower J., Brennan P., Brown N., Chapman T., Drysdale M., Gilbert I.H., Hoelder S., Jordan A., Ley S.V., Merritt A., Miller D., Swarbrick M.E., et. al.
Drug Discovery Today,
2013
13.
Paterson I., Anderson E.A.
Science,
2005
14.
Cuenda A., Sanz-Ezquerro J.J.
Trends in Biochemical Sciences,
2017
15.
Over B., Wetzel S., Grütter C., Nakai Y., Renner S., Rauh D., Waldmann H.
Nature Chemistry,
2012
16.
17.
10.1016/j.mencom.2022.09.041_b0080
Al-Mousawi
J. Chem. Res., Synop.,
1997
18.
Chebanov V.A., Sakhno Y.I., Desenko S.M., Chernenko V.N., Musatov V.I., Shishkina S.V., Shishkin O.V., Kappe C.O.
Tetrahedron,
2007
19.
Quiroga J., Hormaza A., Insuasty B., Saitz C., Cañete A., Jullian C.
Journal of Heterocyclic Chemistry,
1998
20.
Quiroga J., Hormaza A., Insuasty B., Márquez M.
Journal of Heterocyclic Chemistry,
1998
21.
Quiroga J., Insuasty B., Hormaza A., Cabildo P., Claramunt R.M., Elguero J.
Heterocyclic Communications,
1999
22.
El-borai M.A., Rizk H.F., Abd-Aal M.F., El-Deeb I.Y.
European Journal of Medicinal Chemistry,
2012
23.
Vasantha V.A., Jana S., Parthiban A., Vancso J.G.
Chemical Communications,
2014
24.
Liu N., Wang Y., Huang G., Ji C., Fan W., Li H., Cheng Y., Tian H.
Bioorganic Chemistry,
2016
25.
Cappelli A., Nannicini C., Gallelli A., Giuliani G., Valenti S., Mohr G.L., Anzini M., Mennuni L., Ferrari F., Caselli G., Giordani A., Peris W., Makovec F., Giorgi G., Vomero S., et. al.
Journal of Medicinal Chemistry,
2008
26.
10.1016/j.mencom.2022.09.041_b0115
Fathy
J. Chem. Pharm. Res.,
2015
27.
Lavecchia G., Berteina-Raboin S., Guillaumet G.
Tetrahedron Letters,
2004
28.
10.1016/j.mencom.2022.09.041_b0125
Panchal
Int. J. Appl. Eng. Res.,
2019
29.
Vandyshev D.Y., Shikhaliev K.S., Kokonova A.V., Potapov A.Y., Kolpakova M.G., Sabynin A.L., Zubkov F.I.
Chemistry of Heterocyclic Compounds,
2016
30.
Vandyshev D.Y., Shikhaliev K.S., Potapov A.Y., Krysin M.Y., Zubkov F.I., Sapronova L.V.
Beilstein Journal of Organic Chemistry,
2017
31.
Kovygin Y.A., Shikhaliev K.S., Krysin M.Y., Potapov A.Y., Ledenyova I.V., Kosheleva Y.A., Vandyshev D.Y.
Chemistry of Heterocyclic Compounds,
2019
32.
33.
Ferris R.G., Hazen R.J., Roberts G.B., St. Clair M.H., Chan J.H., Romines K.R., Freeman G.A., Tidwell J.H., Schaller L.T., Cowan J.R., Short S.A., Weaver K.L., Selleseth D.W., Moniri K.R., Boone L.R., et. al.
Antimicrobial Agents and Chemotherapy,
2005
34.
Gu S., Zhang X., He Q., Yang L., Ma X., Zheng Y., Yang S., Chen F.
Bioorganic and Medicinal Chemistry,
2011