Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

Oleksandr O. Stepaniuk; Tymofii V. Rudenko; Bohdan V. Vashchenko; Vitalii O. Matvienko; Ivan S. Kondratov; Andrey A. Tolmachev; Oleksandr O. Grygorenko

doi:10.1055/s-0039-1707987

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(13): 1915-1926
DOI: 10.1055/s-0039-1707987

paper

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

Oleksandr O. Stepaniuk

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine eMail: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine eMail: gregor@univ.kiev.ua

,

Tymofii V. Rudenko

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine eMail: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine eMail: gregor@univ.kiev.ua

,

Bohdan V. Vashchenko

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine eMail: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine eMail: gregor@univ.kiev.ua

,

Vitalii O. Matvienko

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine eMail: kondratov@mail.enamine.net

,

Ivan S. Kondratov∗

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine eMail: kondratov@mail.enamine.net

^сV. P. Kukhar Institute of Bioorganic Chemistry & Petrochemistry, NAS of Ukraine, Murmanska Street 1, Kyiv 02660, Ukraine

,

Andrey A. Tolmachev

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine eMail: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine eMail: gregor@univ.kiev.ua

,

Oleksandr O. Grygorenko ∗

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine eMail: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine eMail: gregor@univ.kiev.ua

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Abstract

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Abstract

An efficient approach to the preparation of pyridine carboxylates fused with 5- or 6-membered heteroaromatic rings is described. The method relied on the Combes-type condensation of the low-molecular-weight β-alkoxyvinyl glyoxylates as CCC bis-electrophiles and with heteroaromatic amines as NCC binucleophiles. In most experiments, β-alkoxyvinyl glyoxylates without additional substituent at the β position led to the corresponding α-pyridine carboxylates (67–87% yield). In the case of β-methyl-substituted derivative, γ-pyridine carboxylates were obtained in 84–99% yield. It was found that regioselectivity of the condensation could be efficiently tuned by changing conditions, such as solvents and acidic additives (HOAc, DMSO or HCl–1,4-dioxane).

Key words

nitrogen heterocycles - fused pyridine - amino heterocycles - glyoxylates - condensation - regioselectivity

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References
1 Mousseau JJ, Bull JA, Ladd CL, Fortier A, Sustac Roman D, Charette AB. J. Org. Chem. 2011; 76: 8243
2 Gunasekaran P, Indumathi S, Perumal S. RSC Adv. 2013; 3: 8318
3 Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
4 Sharma PK, Singh K, Kumar S, Kumar P, Dhawan SN, Lal S, Ulbrich H, Dannhardt G. Med. Chem. Res. 2011; 20: 239
5 Lynch BM, Khan MA, Teo HC, Pedrotti F. Can. J. Chem. 1988; 66: 420
6 Gunasekaran P, Prasanna P, Perumal S. Tetrahedron Lett. 2014; 55: 329
7 Kim HS, Jadhav JR, Jung SJ, Kwak JH. Bioorg. Med. Chem. Lett. 2013; 23: 4315
8 Pagadala R, Maddila S, Moodley V, Van Zyl WE, Jonnalagadda SB. Tetrahedron Lett. 2014; 55: 4006
9 Huang S, Lin R, Yu Y, Lu Y, Connolly PJ, Chiu G, Li S, Emanuel SL, Middleton SA. Bioorg. Med. Chem. Lett. 2007; 17: 1243
10 Höhn H, Denzel T, Janssen W. J. Heterocycl. Chem. 1972; 9: 235
11 Denzel T, Höhn H. Arch. Pharm. 1976; 309: 486
12 Misra RN, Rawlins DB, Xiao HY, Shan W, Bursuker I, Kellar KA, Mulheron JG, Sack JS, Tokarski JS, Kimball SD, Webster KR. Bioorg. Med. Chem. Lett. 2003; 13: 1133
13 Roecker AJ, Reger TS, Mattern MC, Mercer SP, Bergman JM, Schreier JD, Cube RV, Cox CD, Li D, Lemaire W, Bruno JG, Harrell CM, Garson SL, Gotter AL, Fox SV, Stevens J, Tannenbaum PL, Prueksaritanont T, Cabalu TD, Cui D, Stellabott J, Hartman GD, Young SD, Winrow CJ, Renger JJ, Coleman PJ. Bioorg. Med. Chem. Lett. 2014; 24: 4884
14 Vacca JP, Wan B.-L, Anthony NJ, Su D.-S, Perlow-Poehnelt R, Felock PJ, Bahnck C, Lai M.-T, Miller M, Rudd D, Lu M, Williams TM, Lim JJ, Munshi V, Tinney E, Anderson KD, Sanchez R, Flynn JA, DiStefano DJ, Touch S, Moyer G, Young MB, Liang Y. J. Med. Chem. 2009; 52: 7163
15 Shimizu Y, Yoshimi K, Sakai J, Kojima K, Kaneko I, Kozuka M, Iwata N, Iizawa T. Jpn. J. Pharmacol. 2002; 88: 174
16 Edupuganti R, Wang Q, Tavares CD. J, Chitjian CA, Bachman JL, Ren P, Anslyn EV, Dalby KN. Bioorg. Med. Chem. 2014; 22: 4910
17 Stepaniuk OO, Rudenko TV, Vashchenko BV, Matvienko VO, Kondratov IS, Tolmachev AA, Grygorenko OO. Tetrahedron 2019; 75: 3472
18 Ghaedi A, Bardajee GR, Mirshokrayi A, Mahdavi M, Shafiee A, Akbarzadeh T. RSC Adv. 2015; 5: 89652
19 Hamama WS, Ibrahim ME, Zoorob HH. Arch. Pharm. 2012; 345: 468
20 Bubnov NV, Silaichev PS, Maslivets AN, Filimonov VO, Denislamova ES. Russ. J. Org. Chem. 2013; 49: 1248
21 Morozova AD, Muravyova EA, Desenko SM, Musatov VI, Yedamenko DV, Chebanov VA. Chem. Heterocycl. Compd. 2016; 52: 934
22 El-Borai MA, Rizk HF, Abd-Aal MF, El-Deeb IY. Eur. J. Med. Chem. 2012; 48: 92
23 Chebanov VA, Sakhno YI, Desenko SM, Chernenko VN, Musatov VI, Shishkina SV, Shishkin OV, Kappe CO. Tetrahedron 2007; 63: 1229
24 Maqbool T, Nazeer A, Khan MN, Elliott MC, Khan MA, Ashraf M, Nasrullah M, Arshad S, Munawar MA. Asian J. Chem. 2014; 26: 2870
25 Dias LR. S, Santos MB, de Albuquerque S, Castro HC, de Souza AM. T, Freitas AC. C, DiVaio MA. V, Cabral LM, Rodrigues CR. Bioorg. Med. Chem. 2007; 15: 211
26 Irfan A, Ahmad A, Al-Sehemi AG, Basra MA. R, Chughtai AH, Ramzan A, Siddiqui S, Munawar MA, Khan MA, Verpoort F. Med. Chem. Res. 2017; 27: 388
27 Lezana N, Tirapegui C, Vargas V, Carrasco C, Jara P, Galdámez A, Vilches-Herrera M, Becerra-Ruiz M, Nuñez M. Eur. J. Org. Chem. 2018; 4795
28 Dubovtsev AY, Dmitriev MV, Silaichev PS, Antonov DI, Maslivets АN. Synthesis 2017; 49: 2223
29 Hughes DD, Bagley MC. Synlett 2002; 1332
30 Mkrtchyan S, Iaroshenko VO, Dudkin S, Gevorgyan A, Vilches-Herrera M, Ghazaryan G, Volochnyuk DM, Ostrovskyi D, Ahmed Z, Villinger A, Sosnovskikh VY, Langer P. Org. Biomol. Chem. 2010; 8: 5280
31 Giardina GA. M, Artico M, Cavagnera S, Cerri A, Consolandi E, Gagliardi S, Graziani D, Grugni M, Hay DW. P, Luttmann MA, Mena R, Raveglia LF, Rigolio R, Sarau HM, Schmidt DB, Zanoni G, Farina C. Farmaco 1999; 54: 364
32 Sarmah MM, Bhuyan D, Prajapati D. RSC Adv. 2015; 5: 12506
33 Walsh EB, Nai-Jue Z, Fang G, Wamhoff H. Tetrahedron Lett. 1988; 29: 4401
34 Kim JH, Bae JW, Yoon CM, Roh YH, Kim SH, Nam GS. Synth. Commun. 2007; 30: 81
35 Hoon Kim S, Yoon Rho K, Hyup Kim J, Min Yoon C. Heterocycles 1998; 48: 2521
36 Blakemore DC, Castro L, Churcher I, Rees DC, Thomas AW, Wilson DM, Wood A. Nat. Chem. 2018; 10: 383
37 Joule JA, Mills K. Heterocyclic Chemistry, 5th ed. . Wiley-Blackwell; Chichester: 2010
38 Gilchrist TL. Heterocyclic Chemistry, 3rd ed. Addison Wesley; Essex: 1997
39 Kudyakova YS, Bazhin DN, Goryaeva MV, Burgart YV, Saloutin VI. Russ. Chem. Rev. 2014; 83: 120
40 Goryaeva MV, Burgart YV, Ezhikova MA, Kodess MI, Saloutin VI. Beilstein J. Org. Chem. 2015; 11: 385
41 Stepaniuk OO, Matvienko VO, Kondratov IS, Shishkin OV, Volochnyuk DM, Mykhailiuk PK, Tolmachev AA. Synthesis 2012; 44: 895
42 Stepaniuk OO, Matviienko VO, Kondratov IS, Vitruk IV, Tolmachev AO. Synthesis 2013; 45: 925
43 Bugera MY, Tarasenko KV, Kondratov IS, Gerus II, Vashchenko BV, Ivasyshyn VE, Grygorenko OO. Eur. J. Org. Chem. 2020; 1069
44 Demchuk OP, Hryshchuk OV, Vashchenko BV, Radchenko DS, Kovtunenko VO, Komarov IV, Grygorenko OO. Eur. J. Org. Chem. 2019; 5937
45 Cherepakha AY, Stepannikova KO, Vashchenko BV, Gorichko MV, Tolmachev AA, Grygorenko OO. Eur. J. Org. Chem. 2018; 6682
46 Subota AI, Lutsenko AO, Vashchenko BV, Volochnyuk DM, Levchenko V, Dmytriv YV, Rusanov EB, Gorlova AO, Ryabukhin SV, Grygorenko OO. Eur. J. Org. Chem. 2019; 3636
47 Subota AI, Ryabukhin SV, Gorlova AO, Grygorenko OO, Volochnyuk DM. J. Fluorine Chem. 2019; 224: 61
48 Melnykov KP, Volochnyuk DM, Ryabukhin SV, Rusanov EB, Grygorenko OO. Amino Acids 2019; 51: 255
49 Subota AI, Artamonov OS, Gorlova A, Volochnyuk DM, Grygorenko OO. Tetrahedron Lett. 2017; 58: 1989
50 Volochnyuk DM, Ryabukhin SV, Plaskon AS, Dmytriv YV, Grygorenko OO, Mykhailiuk PK, Krotko DG, Pushechnikov A, Tolmachev AA. J. Comb. Chem. 2010; 12: 510
51 CCDC 1958393 (12ga) and CCDC 1958394 (13gc) 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.
52 Iaroshenko VO, Ostrovskyi D, Miliutina M, Maalik A, Villinger A, Tolmachev A, Volochnyuk DM, Langer P. Adv. Synth. Catal. 2012; 354: 2495
53 Iaroshenko V, Wang Y, Sevenard D, Volochnyuk D. Synthesis 2009; 1851
54 Armarego WL. F, Chai C. Purification of Laboratory Chemicals, 5th ed. Elsevier; Oxford: 2003
55 Kuntz KW, Campbell JE, Keilhack H, Pollock RM, Knutson SK, Porter-Scott M, Richon VM, Sneeringer CJ, Wigle TJ, Allain CJ, Majer CR, Moyer MP, Copeland RA, Chesworth R. J. Med. Chem. 2016; 59: 1556
56 Li M, Dong X, Zhang N, Jérôme F, Gu Y. Green Chem. 2019; 21: 4650

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