Efficient Route for the Synthesis of Diverse Heteroannelated 5-Cyanopyridines

Andrey P. Mityuk; Andrii Hrebonkin; Pavlo S. Lebed; Galyna P. Grabchuk; Dmitriy M. Volochnyuk; Sergey V. Ryabukhin

doi:10.1055/a-1360-9852

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(12): 2133-2141
DOI: 10.1055/a-1360-9852

paper

Efficient Route for the Synthesis of Diverse Heteroannelated 5-Cyanopyridines

Autor*innen

Andrey P. Mityuk

^aEnamine Ltd., 78 Chervonotkatska str., Kyiv, Ukraine
Andrii Hrebonkin

^aEnamine Ltd., 78 Chervonotkatska str., Kyiv, Ukraine
Pavlo S. Lebed

^aEnamine Ltd., 78 Chervonotkatska str., Kyiv, Ukraine

^bTaras Shevchenko National University of Kyiv, 60 Volodymyrska str., Kyiv, Ukraine
Galyna P. Grabchuk

^bTaras Shevchenko National University of Kyiv, 60 Volodymyrska str., Kyiv, Ukraine
Dmitriy M. Volochnyuk∗

^aEnamine Ltd., 78 Chervonotkatska str., Kyiv, Ukraine

^bTaras Shevchenko National University of Kyiv, 60 Volodymyrska str., Kyiv, Ukraine

^cInstitute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska str., Kyiv, Ukraine
Sergey V. Ryabukhin ∗

^aEnamine Ltd., 78 Chervonotkatska str., Kyiv, Ukraine

^bTaras Shevchenko National University of Kyiv, 60 Volodymyrska str., Kyiv, Ukraine

Abstract

Alle Artikel dieser Rubrik

Abstract

The new efficient, convenient protocol for the synthesis of heteroannelated 3-cyanopyridines and pyrimidines starting from diverse aminoheterocycles and 3,3-dimethoxy-2-formylpropionitrile sodium salt was elaborated. The advantages and improvements of the procedure compared to previously known methods are shown. The scope and limitations of the method are determined. The impact of the structural features on regioselectivity are discussed. The preparativeness, scalability, and application scope of the elaborated protocol are demonstrated by the synthesis of five heteroannelated 3-cyanopyridines in quantities up to 100 grams.

Key words

aminoheterocycles - heterocyclization - heteroannelated 3-cyanopyridines - heteroannelated 3-cyanopyrimidines - 2-dimethoxy-3-hydroxyacrylonitrile

Volltext

Referenzen

References

1a Chrovian CC, Soyode-Johnson A, Wall JL, Rech JC, Schoellerman J, Lord B, Coe KJ, Carruthers NI, Nguyen L, Jiang X, Koudriakova T, Balana B, Letavic MA. ACS Med. Chem. Lett. 2019; 10: 261
1b Lin C, Hulpia F, Da Silva CF, Batista DD. G. J, Van Hecke K, Maes L, Caljon G, Soeiro MD. N. C, Van Calenbergh S. J. Med. Chem. 2019; 62: 8847
1c Manetti F, Schenone S, Bondavalli F, Brullo C, Bruno O, Ranise A, Mosti L, Menozzi G, Fossa P, Trincavelli ML, Martini C, Martinelli A, Tintori C, Botta M. J. Med. Chem. 2005; 48: 7172
1d Santhosh Kumar G, Poornachandra Y, Kumar Gunda S, Ratnakar Reddy K, Mohmed J, Shaik K, Ganesh Kumar C, Narsaiah B. Bioorg. Med. Chem. Lett. 2018; 28: 2328

2 Bell J. Clin. Drug Invest. 2005; 25: 555
3 Adib M, Peytam F, Rahmanian-Jazi M, Mohammadi-Khanaposhtani M, Mahernia S, Bijanzadeh HR, Jahani M, Imanparast S, Faramarzi MA, Mahdavi M, Larijani B. New J. Chem. 2018; 42: 17268

4a Prakash O, Hussain K, Aneja DK, Sharma C, Aneja KR. Org. Med. Chem. Lett. 2011; 1: 1
4b Diacon AH, Pym A, Grobusch M, Patienta R, Rustomjee R, Page-Shipp L, Pistorius C, Krause R, Bogoshi M, Churchyard G, Venter A, Allen J, Palomino JC, De Marez T, van Heeswijk RP. G, Lounis N, Meyvisch P, Verbeeck J, Parys W, de Beule K, Andries K, McNeeley DF. New Engl. J. Med. 2009; 360: 2397

5 Gao F, Liang Y, Zhou P, Cheng J, Ding K, Wang Y. Eur. J. Med. Chem. 2019; 178: 177

6a Trofymchuk SA, Kliukovskyi DV, Semenov SV, Khairulin AR, Shevchenko VO, Bugera MY, Tarasenko KV, Volochnyuk DM, Ryabukhin SV. Synlett 2020; 31: 565
6b Tereshchenko OD, Perebiynis MY, Knysh IV, Vasylets OV, Sorochenko AA, Slobodyanyuk EY, Rusanov EB, Borysov OV, Kolotilov SV, Ryabukhin SV, Volochnyuk DM. Adv. Synth. Catal. 2020; 362: 3229
6c Chernykh AV, Melnykov KP, Tolmacheva NA, Kondratov IS, Radchenko DS, Daniliuc CG, Volochnyuk DM, Ryabukhin SV, Kuchkovska YO, Grygorenko OO. J. Org. Chem. 2019; 84: 8487
6d Melnykov KP, Artemenko AN, Ivanenko BO, Sokolenko YM, Nosik PS, Ostapchuk EN, Grygorenko OO, Volochnyuk DM, Ryabukhin SV. ACS Omega 2019; 4: 7498
6e Nosik PS, Poturai AS, Pashko MO, Melnykov KP, Ryabukhin SV, Volochnyuk DM, Grygorenko OO. Eur. J. Org. Chem. 2019; 4311
6f Feskov IO, Chernykh AV, Kuchkovska YO, Daniliuc CG, Kondratov IS, Grygorenko OO. J. Org. Chem. 2019; 84: 1363

7 Schaefer FC. In The Chemistry of the Cyano Group: Nitrile Reactivity. Rappoport Z. Inter Science; New York: 1970: 239
8 North M. Comprehensive Organic Functional Group Transformations II, Vol. 3. Katritzky A, Taylor R. Elsevier; Amsterdam: 2004: 621
9 Iaroshenko VO, Mkrtchyan S, Volochnyuk DM, Langer P, Sosnovskikh VY, Ostrovskyi D, Dudkin S, Kotljarov AV, Miliutina M, Savych I, Tolmachev AA. Synthesis 2010; 2749

10a Mityuk AP, Volochnyuk DM, Ryabukhin SV, Plaskon AS, Shivanyuk A, Tolmachev AA. Synthesis 2009; 1858
10b Ryabukhin SV, Plaskon AS, Volochnyuk DM, Tolmachev AA. Synthesis 2007; 1861
10c Ryabukhin SV, Plaskon AS, Volochnyuk DM, Tolmachev AA. Synthesis 2007; 3155
10d Ryabukhin SV, Plaskon AS, Volochnyuk DM, Pipko SE, Tolmachev AA. Heterocycles 2008; 75: 583
10e Plaskon AS, Ryabukhin SV, Volochnyuk DM, Shivanyuk AN, Tolmachev AA. Heterocycles 2008; 75: 1765
10f Plaskon AS, Ryabukhin SV, Volochnyuk DM, Gavrilenko KS, Shivanyuk AN, Tolmachev AA. J. Org. Chem. 2008; 73: 6010
10g Plaskon AS, Ryabukhin SV, Volochnyuk DM, Tolmachev AA. Synthesis 2008; 1069
10h Volochnyuk DM, Ryabukhin SV, Plaskon AS, Dmytriv YV, Grygorenko OO, Mykhailiuk PK, Krotko DG, Pushechnikov A, Tolmachev AA. J. Comb. Chem. 2010; 12: 510
10i Ryabukhin SV, Naumchik VS, Grygorenko OO, Tolmachev AA. J. Heterocycl. Chem. 2012; 49: 1147

11 Le Vacher V, Leroy C, Dupas G, Bourguignon J, QuéGuiner G. Synth. Commun. 1994; 24: 2697
12 Benoit R, Dupas G, Bourguignon J, Quéguiner G. Synthesis 1987; 1124

13a Iaroshenko VO, Ostrovskyi D, Miliutina M, Maalik A, Villinger A, Tolmachev A, Volochnyuk DM, Langer P. Adv. Synth. Catal. 2012; 354: 2495
13b Iaroshenko VO, Gevorgyan A, Mkrtchyan S, Grigoryan T, Movsisyan E, Villinger A, Langer P. ChemCatChem 2015; 7: 316

14 Taylor EC, Yoon C. Synth. Commun. 1988; 18: 1187

15a Alekseyev RS, Amirova SS, Terenin VI. J. Heterocycl. Chem. 2017; 54: 2656
15b Barl NM, Sansiaume-Dagousset E, Karaghiosoff K, Knochel P. Angew. Chem. Int. Ed. 2013; 52: 10093
15c Nisha, Bhargava G, Kumar Y. ChemistrySelect 2017; 2: 7827
15d Debenham SD, Chan A, Liu K, Price K, Wood HB. Tetrahedron Lett. 2005; 46: 2283

16 CCDC 2006835 contains the supplementary crystallographic data for compound 5f. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
17 Paek SY, Lee SB, Park DS, Lee WH. WO2014129796A1, 2014
18 Walsh EB, Wamhoff H. Chem. Ber. 1989; 122: 1673
19 Charpentier P, Lobregat V, Levacher V, Dupas G, Queguiner G, Bourguignon J. Tetrahedron Lett. 1998; 39: 4013
20 Duncia JV, Gardner DS, Hynes J, Macor JE, Santella JB, Wu H, Nair SK, Paidi VR, Sarkunam K, Sistla RK, Polimera SR. WO2016210037A1, 2016
21 Baram SG, Shkurko OP, Mamaev VP. Bull. Acad. Sci. USSR 1983; 32: 265

Zusatzmaterial