Synthesis of New Pyrazolo[1,5-a]pyrimidines by Reaction of β,γ-Unsaturated γ-Alkoxy-α-keto Esters with N-Unsubstituted 5-Aminopyrazoles

Oleksandr O. Stepaniuk; Vitalii O. Matviienko; Ivan S. Kondratov; Igor V. Vitruk; Andrei O. Tolmachev

doi:10.1055/s-0032-1318329

Synthesis, Table of Contents

Synthesis 2013; 45(7): 925-930
DOI: 10.1055/s-0032-1318329

paper

Synthesis of New Pyrazolo[1,5-a]pyrimidines by Reaction of β,γ-Unsaturated γ-Alkoxy-α-keto Esters with N-Unsubstituted 5-Aminopyrazoles

Oleksandr O. Stepaniuk

^aKyiv National Taras Shevchenko University, 64 Volodymirska st., 01033 Kyiv-33, Ukraine

^bEnamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine

,

Vitalii O. Matviienko

^aKyiv National Taras Shevchenko University, 64 Volodymirska st., 01033 Kyiv-33, Ukraine

^bEnamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine

,

Ivan S. Kondratov*

^bEnamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine

^cInstitute of Bioorganic Chemistry and Petrochemistry, National Ukrainian Academy of Science, Murmanska 1, 02660 Kyiv-94, Ukraine Fax: +380(44)537325 Email: vanya_ko@mail.ru

,

Igor V. Vitruk

^aKyiv National Taras Shevchenko University, 64 Volodymirska st., 01033 Kyiv-33, Ukraine

^bEnamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine

,

Andrei O. Tolmachev

^aKyiv National Taras Shevchenko University, 64 Volodymirska st., 01033 Kyiv-33, Ukraine

^bEnamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine

› Author Affiliations

Abstract

All articles of this category

Abstract

The reaction of β,γ-unsaturated γ-alkoxy-α-keto esters with N-unsubstituted 5-aminopyrazoles was investigated. The reaction proceeds with high regioselectivity and is considered as an effective method for the preparation of new pyrazolo[1,5-a]pyrimidines bearing an ester function in the 7-position. The obtained drug-like compounds have a great potential for medicinal chemistry as they closely resemble the structure of several marketed pharmaceuticals.

Key words

heterocycles - esters - regioselectivity - pyrazolo[1,5-a]pyrimidines - 5-aminopyrazoles

Full Text

References

References

1a Tietze L.-F, Meier H, Voß E. Synthesis 1988; 274
1b Colla A, Martins MA. P, Clar G, Krimmer S, Fischer P. Synthesis 1991; 483
1c Hojo M, Masuda R, Kokuryo Y, Shioda H, Matsuo S. Chem. Lett. 1976; 499
1d Hojo M, Masuda R, Okada E. Synthesis 1986; 1013
1e Tarasenko KV, Manoylenko OV, Kukhar VP, Röschenthaler G.-V, Gerus II. Tetrahedron Lett. 2010; 51: 4623
1f Effenberger F, Maier R, Schönwälder K.-H, Ziegler T. Chem. Ber. 1982; 115: 2766
1g Mamat C, Pundt T, Schmidt A, Langer P. Tetrahedron Lett. 2006; 47: 2183

For recent examples, see:

2a Zanatta N, Schneider JM. F. M, Schneider PH, Wouters AD, Bonacorso HG, Martins MA. P, Wessjohann LA. J. Org. Chem. 2006; 71: 6996
2b Zanatta N, Amaral SS, Esteves-Souza A, Echevarria A, Brondani PB, Flores DC, Bonacorso HG, Flores AF. C, Martins MA. P. Synthesis 2006; 2305
2c Tolmachova NA, Gerus II, Vdovenko SI, Haufe G, Kirzhner YA. Synthesis 2007; 3797
2d Iaroshenko VO, Volochnyuk DM, Kryvokhyzha NV, Martyloga A, Sevenard DV, Groth U, Brand J, Chernega AN, Shivanyuk AN, Tolmachev AA. Synthesis 2008; 2337
2e Zanatta N, Fantinel L, Lourega RV, Bonacorso HG, Martins MA. P. Synthesis 2008; 358
2f Martins MA. P, Muraro P, Beck P, Machado P, Frizzo CP, Zanatta N, Bonacorso HG. Synth. Commun. 2008; 38: 3465
2g Zanatta N, Faoro D, da S Fernandes L, Brondani PB, Flores DC, Flores AF. C, Bonacorso HG, Martins MA. P. Eur. J. Org. Chem. 2008; 5832
2h Zanatta N, Madruga CC, Marisco PC, da Rosa LS, da Silva FM, Bonacorso HG, Martins MA. P. J. Heterocycl. Chem. 2010; 47: 1234
2i Moreira DN, Frizzo CP, Longhi K, Soares AB, Morzari MR. B, Buriol L, Brondani S, Zanatta N, Bonacorso HG, Martins MA. P. Monatsh. Chem. 2011; 142: 1265
2j Xin Y, Zhao J, Gu J, Zhu S. J. Fluorine Chem. 2011; 132: 402
2k Xin Y, Zhao J, Zhu S. J. Fluorine Chem. 2012; 133: 98

See for example:

3a Frizzo CP, Martins MA. P, Marzari MR. B, Campos PT, Claramunt RM, García MA, Sanz D, Alkorta I, Elguero J. J. Heterocycl. Chem. 2010; 47: 1259
3b Moreira DN, Frizzo CP, Longhi K, Zanatta N, Bonacorso HG, Martins MA. P. Monatsh. Chem. 2008; 139: 1049
3c Nesi R, Chimichi S, Scotton M, Degl’Innocenti A, Adembri G. J. Chem. Soc., Perkin Trans. 1 1980; 1667
3d Dyachenko VD, Tkachev RP, Dyachenko AD. Russ. J. Gen. Chem. 2009; 79: 121
3e Machado P, Rosa FA, Rossatto M, Sant’Anna G.da S, Sauzem PD, Siqueira da Silva RM, Rubin MA, Ferreira J, Bonacorso HG, Zanatta N, Martins MA. P. ARKIVOC 2007; (xvi): 281

4 Stepaniuk OO, Matvienko VO, Kondratov IS, Shishkin OV, Volochnyuk DM, Mykhailiuk PK, Tolmachev AA. Synthesis 2012; 44: 895
5 Saito T, Obitsu T, Minamoto C, Sugiura T, Matsumura N, Ueno S, Kishi A, Katsumata S, Nakai H, Toda M. Bioorg. Med. Chem. 2011; 19: 5955

6a Wegner F, Deuter-Conrad W, Scheunemann M, Brust P, Fischer S, Hiller A, Diekers M, Strecker K, Wohlfarth K, Allgaier C, Steinbach J, Hoepping A. Eur. J. Pharmacol. 2008; 580: 1
6b Hoepping A, Diekers M, Deuther-Conrad W, Scheunemann M, Fischer S, Hiller A, Wegner F, Steinbach J, Brust P. Bioorg. Med. Chem. 2008; 16: 1184

7 Griffith DA, Hargrove DM, Maurer TS, Blum CA, De Lombaert S, Inthavongsay JK, Klade LE, Mack CM, Rose CR, Sanders MJ, Carpino PA. Bioorg. Med. Chem. Lett. 2011; 21: 2641
8 Gentles RG, Hu S, Huang Y, Grant-Young K, Poss MA, Andres C, Fiedler T, Knox R, Lodge N, Weaver D, Harden DG. Bioorg. Med. Chem. Lett. 2008; 18: 5694
9 Zhou H.-B, Sheng S, Compton DR, Kim Y, Joachimiak A, Sharma S, Carlson KE, Katzenellenbogen BS, Nettles KW, Greene GL, Katzenellenbogen JA. J. Med. Chem. 2007; 50: 399
10 Altenbach RJ, Liu H, Banfor PN, Browman KE, Fox GB, Fryer RM, Komater VA, Krueger KM, Marsh K, Miller TR, Pan JB, Pan L, Sun M, Thiffault C, Wetter J, Zhao C, Zhou D, Esbenshade TA, Hancock AA, Cowart MD. J. Med. Chem. 2007; 50: 5439
11 Shen HC, Taggart AK. P, Wilsie LC, Waters MG, Hammond ML, Tata JR, Colletti SL. Bioorg. Med. Chem. Lett. 2008; 18: 4948
12 Frey RR, Curtin ML, Albert DH, Glaser KB, Pease LJ, Soni NB, Bouska JJ, Reuter D, Stewart KD, Marcotte P, Bukofzer G, Li J, Davidsen SK, Michaelides MR. J. Med. Chem. 2008; 51: 3777
13 Heathcote DA, Patel H, Kroll SH. B, Hazel P, Periysamy M, Alikian M, Kanneganti SK, Jogalekar AS, Scheiper B, Barbazanges M, Blum A, Brackow J, Siwicka A, Pace RD. M, Fuchter MJ, Snyder JP, Liotta DC, Freemont PS, Aboagye EO, Coombers RC, Barrett AG. M, Ali S. J. Med. Chem. 2010; 53: 8508
14 Mukaiyama H, Nishimura T, Kobayashi S, Komatsu Y, Kikuchi S, Ozawa T, Kamada N, Ohnota H. Bioorg. Med. Chem. 2008; 16: 909
15 Ren L, Laird ER, Buckmelter AJ, Dinkel V, Gloor SL, Grina J, Newhouse B, Rasor K, Hastings G, Gradl SN, Rudolph J. Bioorg. Med. Chem. Lett. 2012; 22: 1165
16 Labroli M, Paruch K, Dwyer MP, Alvares C, Keertikar K, Poker C, Rossman R, Duca JS, Fischmann TO, Madison V, Parry D, Davis N, Seghezzi W, Wiswell D, Guzi TJ. Bioorg. Med. Chem. Lett. 2011; 21: 471
17 Kosugi T, Mitchel DR, Fujino A, Imai M, Kambe M, Kobayashi S, Makino H, Matsueda Y, Oue Y, Komatsu K, Imaizumi K, Sakai Y, Sugiura S, Takenouchi O, Unoki G, Yamakoshi Y, Cunliffe V, Suzuki N, Takimoto-Kamimura M, Frearson J, Gordon R, Harris CJ, Kalloo-Hosein H, Le J, Patel G, Simpson DJ, Sherborne B, Thomas PS, Kataoka K. J. Med. Chem. 2012; 55: 6700
18 Gommerman N, Buehlmayer P, Von Matt A, Breitenstein W, Masuya K, Pirard B, Furet P, Cowan-Jacob SW, Weckbecker G. Bioorg. Med. Chem. Lett. 2010; 20: 3628
19 Cuny GD, Yu PB, Laha JK, Xing X, Liu J.-F, Lai CS, Deng DY, Sachidanandan C, Bloch KD, Peterson RT. Bioorg. Med. Chem. Lett. 2008; 18: 4388
20 Kato N, Oka M, Murase T, Yoshida M, Sakairi M, Yamashita S, Yasuda Y, Yoshikawa A, Hayashi Y, Makino M, Takeda M, Mirensha Y, Kakigami T. Bioorg. Med. Chem. 2011; 19: 7221
21 Shaaban MR, Saleh TS, Mayhoub AS, Mansour A, Farag AM. Bioorg. Med. Chem. 2008; 16: 6344
22 Wang YD, Honores E, Wu B, Johnson S, Powell D, Miranda M, McGinnis JP, Discafani C, Rabindran SK, Cheng W, Krishnamurthy G. Bioorg. Med. Chem. 2009; 17: 2091

23a Popovici-Muller J, Shipps GW. Jr, Rosner KE, Deng Y, Wang T, Curran PJ, Brown MA, Siddiqui MA, Cooper AB, Duca J, Cable M, Girijavallabhan V. Bioorg. Med. Chem. Lett. 2009; 19: 6331
23b Gudmundsson KS, Johns BA, Weatherhead J. Bioorg. Med. Chem. Lett. 2009; 19: 5689

24a Gregg BT, Tymoshenko DO, Razzano DA, Johnson MR. J. Comb. Chem. 2007; 9: 507
24b Sagar R, Park SB. J. Org. Chem. 2008; 73: 3270

For recent examples, see:

25a Emelina EE, Petrov AA, Firsov AV. Russ. J. Org. Chem. 2007; 43: 471
25b Petrov AA, Kasatochkin AN, Emelina EE, Nelyubina YuV, Antipin MYu. Russ. J. Org. Chem. 2009; 45: 1390
25c Emelina EE, Petrov AA, Selivanov SI, Nelyubina YuV, Antipin MYu. J. Fluorine Chem. 2009; 130: 861
25d Ivachtchenko AV, Dmitriev DE, Golovina ES, Kadieva MG, Koryakova AG, Kysil VM, Mitkin OD, Okun IM, Tkachenko SE, Vorobiev AA. J. Med. Chem. 2010; 53: 5186
25e Yoshida M, Mori A, Inaba A, Oka M, Makino H, Yamaguchi M, Fujita H, Kawamoto T, Goto M, Kimura H, Baba A, Yasuma T. Bioorg. Med. Chem. 2010; 18: 8501
25f Ivachtchenko AV, Golovina ES, Kadieva MG, Kysil VM, Mitkin OD, Vorobiev AA, Okun I. Bioorg. Med. Chem. Lett. 2012; 22: 4273

26 Chimichi S, Cosimelli B, Bruni F, Selleri S. Magn. Reson. Chem. 1992; 30: 1117

Supplementary Material

Supporting Information