2-Carbamimidoylbenzoic Acid as a New Effective and Available Precursor for the Synthesis of Substituted 2-(Pyrimidin-2-yl)benzoic Acids

Volodymyr A. Tkachuk; Vyacheslav O. Shishkanu; Tetiana M. Tkachuk; Svitlana V. Shishkina; Olga V. Hordiyenko

doi:10.1055/s-0040-1705941

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(02): 371-382
DOI: 10.1055/s-0040-1705941

paper

2-Carbamimidoylbenzoic Acid as a New Effective and Available Precursor for the Synthesis of Substituted 2-(Pyrimidin-2-yl)benzoic Acids

Autoren

Volodymyr A. Tkachuk

^aTaras Shevchenko National University of Kyiv, Faculty of Chemistry, 64/13 Volodymyrs’ka Str., Kyiv 01601, Ukraine eMail: ov_hordiyenko@chem.knu.ua
Vyacheslav O. Shishkanu

^aTaras Shevchenko National University of Kyiv, Faculty of Chemistry, 64/13 Volodymyrs’ka Str., Kyiv 01601, Ukraine eMail: ov_hordiyenko@chem.knu.ua
Tetiana M. Tkachuk

^bSMC Ecopharm Ltd, 136-B Naberezhno-Korchuvatska Str., Kyiv 03045, Ukraine
Svitlana V. Shishkina

^cSSI ‘Institute for Single Crystals’ of National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine
Olga V. Hordiyenko ∗

^aTaras Shevchenko National University of Kyiv, Faculty of Chemistry, 64/13 Volodymyrs’ka Str., Kyiv 01601, Ukraine eMail: ov_hordiyenko@chem.knu.ua

Abstract

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Abstract

A new approach to the synthesis of 2-(pyrimidin-2-yl)benzoic acids based on the ring contraction of the 2-carbamimidoylbenzoic acid [(2-amidinobenzoic) acid] with 1,3-dicarbonyl compounds and their synthetic equivalents has been developed. The intramolecular condensation of the obtained acids with 1,3-dielectrophiles proceeds with the formation of the 4,6-dihydropyrimido[2,1-a]isoindole-4,6-dione system, the pyrrolidone ring of which is easily opened under the action of weak nucleophiles. The reaction of 2-amidinobenzoic acid with chromones, which have an aryloxy group at 3-position does not stop at the step of pyrimidine ring formation and undergoes further spontaneous cyclization into 2-(benzo[4,5]furo[3,2-d]pyrimidin-2-yl)benzoic acids.

Key words

2-carbamimidoylbenzoic acid - ring closure - 2-(pyrimidin-2-yl)benzoic acids - 4,6-dihydropyrimido[2,1-a]isoindole-4,6-dione - chromone ring opening - green chemistry

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Referenzen

References
1 Jain KS, Arya N, Inamdar NN, Auti PB, Unawane SA, Puranik HH, Sanap MS, Inamke AD, Mahale VJ, Prajapati CS, Shishoo CJ. Curr. Top. Med. Chem. 2016; 16: 3133
2 Large JM, Torr JE, Raynaud FI, Clarke PA, Hayes A, di Stefano F, Urban F, Shuttleworth SJ, Saghir N, Sheldrake P, Workman P, McDonald E. Bioorg. Med. Chem. Lett. 2011; 19: 836
3 Xu Z, Liu Z, Chen T, Chen T, Wang Z, Tian G, Shi J, Wang X, Lu Y, Yan X, Wang G, Jiang H, Chen K, Wang S, Xu Y, Shen J, Zhu W. J. Med. Chem. 2011; 54: 5607
4 Negoro K, Yonetoku Y, Maruyama T, Yoshida S, Takeuchi M, Ohta M. Bioorg. Med. Chem. 2012; 20: 2369
5 Dahlgren MK, Garcia AB, Hare AA, Tirado-Rives J, Leng L, Bucala R, Jorgensen WL. J. Med. Chem. 2012; 55: 10148
6 Uehara F, Shoda A, Aritomo K, Fukunaga K, Watanabe K, Ando R, Shinoda M, Ueno H, Kubodera H, Sunada S, Saito K.-I, Kaji T, Asano S, Eguchi J, Yuki S, Tanaka S, Yoneyama Y, Niwa T. Bioorg. Med. Chem. Lett. 2013; 23: 6928
7 Caroff E, Meyer E, Treibe A, Hilpert K, Riederer MA. Bioorg. Med. Chem. Lett. 2014; 24: 4323
8 Lan Y, Chen Y, Cao X, Zhang J, Wang J, Xu X, Qiu Y, Zhang T, Liu X, Liu B.-F, Zhang G. J. Med. Chem. 2014; 57: 10404
9 Vidal M, García-Arriagada M, Rezende MC, Domínguez M. Synthesis 2016; 48: 4246
10 Gurney ME, Nugent RA, Mo X, Sindac JA, Hagen TJ, Fox DIII, O’Donnell JM, Zhang C, Xu Y, Zhang H.-T, Groppi VE, Bailie M, White RE, Romero DL, Vellekoop AS, Walker JR, Surman MD, Zhu L, Campbell RF. J. Med. Chem. 2019; 62: 4884
11 Krapf MK, Gallus J, Wiese M. J. Med. Chem. 2017; 60: 4474
12 Maurya HK, Gupta A. RSC Adv. 2014; 4: 22106
13 Engel J, Richters A, Getlik M, Tomassi S, Keul M, Termathe M, Lategahn J, Becker C, Mayer-Wrangowski S, Grütter C, Uhlenbrock N, Krüll J, Schaumann N, Eppmann S, Kibies P, Hoffgaard F, Heil J, Menninger S, Ortiz-Cuaran S, Heuckmann J, Tinnefeld V, Zahedi RP, Sos ML, Schultz-Fademrecht C, Thomas RK, Kast SM, Rauh D. J. Med. Chem. 2015; 58: 6844
14 Li X, Shi B, Teng Y, Cheng Y, Yang H, Li J, Wang L, He S, You Q, Xiang H. Med. Chem. Commun. 2019; 10: 294
15 Luo G, Tang Z, Lao K, Li X, You Q, Xiang H. Eur. J. Med. Chem. 2018; 150: 783
16 Filipski KJ, Guzman-Perez A, Bian J, Perreault C, Aspnes GE, Didiuk MT, Dow RL, Hank RF, Jones CS, Maguire RJ, Tu M, Zeng D, Liu S, Knafels JD, Litchfield J, Atkinson K, Derksen DR, Bourbonais F, Gajiwala KS, Hickey M, Johnson TO, Humphries PS, Pfefferkorn JA. Bioorg. Med. Chem. Lett. 2013; 23: 4571
17 Li Q, Hu G, Hu L, Chen Z. Patent CN110305125 A, 2019 ; Chem. Abstr. 2019, 172, 307040.
18 Kim C, Nakai T, Wai-Ho Lee T, Moore J, Perl NR, Rohde J, Iyengar RR, Mermerian A. Patent WO 2012003405 2012 ; Chem. Abstr. 2012, 156, 148433.
19 Almstead N, Karp GM, Wilde R, Welch E, Ren H. Patent WO 2006/044505 A2, 2006 ; Chem. Abstr. 2006, 144, 432841
20 Shaw AN, Duffy KJ, Tedesco R, Wiggall K. US Patent 2008/0171756 A1, 2008 ; Chem. Abstr. 2008, 149, 176630.
21 Alexander RP, Bailey S, Brand S, Brookings DC, Brown JA, Haughan AF, Kinsella N, Lowe C, Mack SR, Pitt WR, Richard MD, Sharpe A, Tait LJ. Patent WO2007/141504 A1, 2007 ; Chem. Abstr. 2007, 148, 54880.
22 Juby PF, Partyka RA. US Patent 4031093, 1977 ; Chem. Abstr. 1977, 87, 102377.

23a Harris RL. N, Huppatz JL, Teitei T. Aust. J. Chem. 1979; 32: 669
23b Reimlinger H, Billiau F, Peiren MA. Merényi R. Chem. Ber. 1972; 105: 108

24a Hordiyenko OV, Biitseva AV, Kostina YuYu, Zubatyuk RI, Shishkin OV, Groth UM, Kornilov MYu. Struct. Chem. 2017; 28: 607
24b Tkachuk VA, Omelchenko IV, Hordiyenko OV. Synlett 2017; 28: 851

25 Gong Y, Pauls HW. Synlett 2000; 829
26 Sato M, Ogasawara H, Kato T. J. Heterocycl. Chem. 1983; 20: 87
27 Coleman PJ, Schreier JD, Cox CD, Breslin MJ, Whitman DB, Bogusky MJ, McGaughey GB, Bednar RA, Lemaire W, Doran SM, Fox SV, Garson SL, Gotter AL, Harrell CM, Reiss DR, Cabalu TD, Cui D, Prueksaritanont T, Stevens J, Tannenbaum PL, Ball RG, Stellabott J, Young SD, Hartman GD, Winrow CJ, Renger JJ. ChemMedChem 2012; 7: 415
28 King FE, King TJ, Muir ІH. M. J. Chem. Soc. 1946; 5
29 Maggiolo A, Phillips AP, Hitchings GH. J. Am. Chem. Soc. 1951; 73: 106
30 Cheung HT. A, Gray PG. J. Labelled Compd. Radiopharm. 1984; 21: 471
31 Dunn AD. J. Heterocycl. Chem. 1984; 21: 965
32 Tkachuk V, Merkulova V, Omelchenko I, Arrault A, Hordiyenko O. Tetrahedron Lett. 2019; 60. 1959
33 Matulková I, Andreoni R, Císařová I, Němec I, Fábry J. Z. Kristallogr. 2017; 232: 471
34 Kenner GW, Lythgoe B, Todd AR, Topham A. J. Chem. Soc. 1943; 388
35 Joule JA, Mills K. Heterocyclic Chemistry, 4th ed. Blackwell Science; Oxford: 2000
36 Babichev FS, Kovtunenko VA, Ishchenko VV, Tyltin AK, Yudina TA. Chem. Heterocycl. Compd. 1985; 21: 1395
37 Gaozza CH, Grinberg H, Lamdan S. J. Heterocycl. Chem. 1972; 9: 883
38 Boyd GV. In The Chemistry of Amidines and Imidates, Vol. 2. Patai S, Rappoport Z. Wiley; New York: 1991: 367
39 Khilya VP, Kornilov MYu, Gorbulenko NV, Golubushina GM, Kovtun EN, Kolotusha NV, Panasenko GV. Chem. Heterocycl. Compd. 1985; 21: 1273

40a Khilya VP, Turov AV, Tkachuk TM, Shevchuk LI. Chem. Nat. Compd. 2001; 37: 307
40b Sosnovskikh VYa, Usachev BI, Sizov AYu, Barabanov MA. Synthesis 2004; 942
40c Frasinyuk MS, Bondarenko SP, Khilya VP. Chem. Nat. Compd. 2006; 42: 673

41 Pivovarenko VG, Tkachuk TM. Ukr. Bioorg. Acta 2005; 2: 22
42 Tkachuk Т. М. J. Org. Pharm. Chem. 2008; 6: 81
43 Vaidya VP, Agasimundin YS. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1981; 20: 114
44 Malik WU, Mahesh VK, Raishighani M. Indian J. Chem. 1971; 9: 655

45a Chang M.-Y, Chen Y.-H, Wang H.-S. J. Org. Chem. 2018; 83: 2361
45b Chao B, Lin S, Ma Q, Lu D, Hu Y. Org. Lett. 2012; 14: 2398
45c Stengel I, Wolleb A, Wolleb H, Heinemeyer U, Nagashima H. Patent WO2015/114102, 2015 ; Chem. Abstr. 2015, 163, 295886.

46 CCDC 1993264 contains 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.
47 Zefirov YuV. Kristallographiya (Russian) 1997; 42: 936
48 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112

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