Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(10): 2223-2230
DOI: 10.1055/s-0036-1588407
DOI: 10.1055/s-0036-1588407
paper
Formal [3+3] Cyclocondensation of 4-Acyl-1H-pyrrole-2,3-diones with Five-Membered Cyclic Enamines To Form Substituted 1H-Pyrazolo[3,4-b]pyridines and Isoxazolo[5,4-b]pyridines
Further Information
Publication History
Received: 19 October 2016
Accepted after revision: 10 January 2017
Publication Date:
31 January 2017 (online)
Abstract
A highly efficient method for the preparation of multifunctional substituted 1H-pyrazolo[3,4-b]pyridines and isoxazolo[5,4-b]pyridines was developed through the formal [3+3] cascade cyclocondensation of 4-acyl-1H-pyrrole-2,3-diones as 1,3-bis-electrophiles with the five-membered cyclic enamines as 1,3-bis-nucleophiles.
Key words
fused-ring systems - nitrogen heterocycles - oxygen heterocycles - synthetic methods - cascade reactionsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588407.
- Supporting Information
-
References
- 1a Neres J, Engelhart CA, Drake EJ, Wilson DJ, Fu P, Boshoff HI, Barry CE, Gulick AM, Aldrich CC. J. Med. Chem. 2013; 56: 2385
- 1b Quiroga J, Diaz Y, Bueno J, Insuasty B, Abonia R, Ortiz A, Nogueras M, Cobo J. Eur. J. Med. Chem. 2014; 74: 216
- 1c McElroy WT, Tan Z, Basu K, Yang S, Smotryski J, Ho GD, Tulshian D, Greenlee WJ, Mullins D, Guzzi M, Zhang X, Bleickardt C, Hodgson R. Bioorg. Med. Chem. Lett. 2012; 22: 1335
- 1d Nascimento-Junior NM, Mendes TC. F, Leal DM, Correa CM. N, Sudo RT, Zapata-Sudo G, Barreiro EJ, Fraga CA. M. Bioorg. Med. Chem. Lett. 2010; 20: 74
- 1e Young R, Glennon RA, Dewey WL. Psychopharmacology 1987; 93: 494
- 1f Drake EJ, Duckworth BP, Neres J, Aldrich CC, Gulick AM. Biochemistry 2010; 49: 9292
- 1g Ehlert FJ, Ragan P, Chen A, Roeske WR, Yamamura HI. Eur. J. Pharmacol. 1982; 78: 249
- 1h Menegatti R, Silva GM. S, Zapata-Sudo G, Raimundo JM, Sudo RT, Barreiroa EJ, Fraga CA. M. Bioorg. Med. Chem. 2006; 14: 632
- 1i Dias LR. S, Santos MB, Albuquerque S, Castro HC, Souza AM. T, Freitas AC. C, DiVaio MA. V, Cabrale LM, Rodrigues CR. Bioorg. Med. Chem. 2007; 15: 211
- 1j Zask A, Gu Y, Albright JD, Du X, Hogan M, Levin JI, Chen JM, Killar LM, Sung A, DiJoseph JF, Sharr MA, Roth CE, Skala S, Jin G, Cowling R, Mohler KM, Barone D, Black R, March C, Skotnicki JS. Bioorg. Med. Chem. Lett. 2003; 13: 1487
- 2 Bhonde VR, O’Neill BT, Buchwald SL. Angew. Chem. Int. Ed. 2016; 55: 1849
- 3a Mackay M, Nortcliffe A, McNab H, Hulme AN. Synthesis 2015; 47: 242
- 3b Wang L, Uramaru N, Wong F. Tetrahedron 2014; 70: 7439
- 4a Hill MD. Synthesis 2016; 48: 2201
- 4b Eissa IH, El-Naggar AM, El-Hashash MA. Bioorg. Chem. 2016; 67: 43
- 4c Tkachenko VV, Muravyova EA, Desenko SM, Shishkin OV, Shishkina SV, Sysoiev DO, Müller TJ. J, Chebanov VA. Beilstein J. Org. Chem. 2014; 10: 3019
- 4d Jiang B, Liu Y, Tu S. Eur. J. Org. Chem. 2011; 16: 3026
- 4e Tabrizi MA, Baraldi PG, Saponaro G, Moorman AR, Romagnoli R, Preti D, Baraldi S, Corciulo C, Vincenzi F, Borea PA, Varani K. J. Med. Chem. 2013; 56: 1098
- 4f Mityuk AP, Kolodych SE, Mytnyk SA, Dmytriv YV, Volochnyuk DM, Mykhailiuk PK, Tolmachev AA. Synthesis 2010; 2767
- 5a Wei H, Zhou C, Ham S, White JM, Birney DM. Org. Lett. 2004; 23: 4289
- 5b Bhanushali M, Zhao C. Tetrahedron Lett. 2012; 53: 359
- 5c George L, Bernhardt PV, Netsch K, Wentrup C. Org. Biomol. Chem. 2004; 2: 3518
- 5d Abd El-Nabi HA. Tetrahedron 2002; 58: 135
- 5e Fabian WM. F. J. Org. Chem. 2002; 67: 7475
- 5f Kappe CO, Kollenz G, Wentrup C. J. Chem. Soc., Chem. Commun. 1992; 485
- 5g Cobas A, Guitian E, Castedo L. J. Org. Chem. 1993; 58: 3113
- 5h Kollenz G, Igel H, Ziegler E. Monatsh. Chem. 1972; 103: 450
- 5i Eistert B, Müller GW, Arackal TJ. Liebigs Ann. Chem. 1976; 1031
- 5j Isobe K, Mohri C, Sano H, Mohri K, Enomoto H, Sano T, Tsuda Y. Chem. Pharm. Bull. 1989; 37: 3236
- 6a Yoshida Y, Mohri K, Isobe K, Itoh T, Yamamoto K. J. Org. Chem. 2009; 74: 6010
- 6b Nimgirawath S, Udomputtimekakul P. Molecules 2009; 14: 917
- 6c Hosoi S, Nagao M, Tsuda Y, Isobe K, Sano T, Ohta T. J. Chem. Soc., Perkin Trans. 1 2000; 1505
- 6d Tsuda Y, Ohshima T, Hosoi S, Kaneuchi S, Kiuchi F, Jun T, Sano T. Chem. Pharm. Bull. 1996; 44: 500
- 6e Saa C, Guitian E, Castedo L. J. Org. Chem. 1986; 51: 2781
- 7a Dubovtsev АYu, Denislamova ES, Dmitriev МV, Maslivets АN. Russ. J. Org. Chem. 2016; 52: 706
- 7b Silaichev PS, Filimonov VO, Slepukhin PA, Maslivets AN. Molecules 2012; 17: 13787
- 7c Bannikova YuN, Maslivets AN. Chem. Heterocycl. Compd. 2004; 40: 118
- 7d Bannikova YuN, Maslivets AN, Rozhkova YuS, Shklyaev YuV, Aliev ZG. Mendeleev Commun. 2005; 15: 158
- 7e Denislamova ES, Maslivets АN. Russ. J. Org. Chem. 2010; 46: 389
- 7f Silaichev PS, Zheleznova MA, Slepukhin PA, Maslivets AN. Russ. J. Org. Chem. 2014; 50: 1594
- 8 Silaichev PS, Bubnov NV, Filimonov VO, Denislamova ES, Maslivets АN. Russ. J. Org. Chem. 2013; 49: 1248
- 9 CCDC-1508473 (10db) and 1508474 (10ne) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.