Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans

Daniil A. Chaplygin; Ivan V. Ananyev; Leonid L. Fershtat; Nina N. Makhova

doi:10.1055/s-0040-1707393

Synthesis, Table of Contents

Synthesis 2020; 52(18): 2667-2678
DOI: 10.1055/s-0040-1707393

paper

Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans

Authors

Daniil A. Chaplygin

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky prosp., 47, Moscow, Russian Federation Email: fershtat@bk.ru
Ivan V. Ananyev

^bA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Vavilova str., 28, Moscow, Russian Federation

^cNational Research University Higher School of Economics, 101000, Moscow, Russian Federation
Leonid L. Fershtat ∗

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky prosp., 47, Moscow, Russian Federation Email: fershtat@bk.ru
Nina N. Makhova

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky prosp., 47, Moscow, Russian Federation Email: fershtat@bk.ru

Abstract

All articles of this category

Abstract

A novel method for the synthesis of a diverse series of functionally substituted five-membered heterocyclic compounds via atom-economic, regio-, and diastereoselective one-pot reaction cascade was developed. This approach involves a ring opening in 4-arylfuroxans to α-oximinoarylacetonitrile oxides followed by [3+2] cycloaddition to various dipolarophiles to afford multisubstituted isoxazoles and isoxazolines. Subsequent azole–azole rearrangement of (oximino)isoxazolines/-isoxazoles, which can be conducted in a one-pot manner, results into functionally substituted furazans formation. The developed protocol is operationally simple, proceeds in mild conditions and with high yields of target heterocyclic systems. Overall, this study represents a new mode of isoxazole and 1,2,5-oxadiazole functionalization strategy, which is useful in medicinal and materials chemistry.

Key words

nitrogen heterocycles - 1,2,5-oxadiazole - rearrangement - cascade reactions - [3+2] cycloaddition

Full Text

References

References

1a Smith JM, Dixon JA, deGruyter JN, Baran PS. J. Med. Chem. 2019; 62: 2256
1b Krska SW, DiRocco DA, Dreher SD, Shevlin M. Acc. Chem. Res. 2017; 50: 2976
1c Liu Y.-J, Xu H, Kong W.-J, Shang M, Dai H.-X, Yu J.-Q. Nature 2014; 515: 389
1d Hansen EC, Pedro DJ, Wotal AC, Gower NJ, Nelson JD, Caron S, Weix DJ. Nat. Chem. 2016; 8: 1126
1e Hilton MC, Zhang X, Boyle BT, Alegre-Requena JV, Paton RS, McNally A. Science 2018; 362 6416, 799

2a Das P, Delost MD, Qureshi MH, Smith DT, Njardarson JT. J. Med. Chem. 2019; 62: 4265
2b Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257

For recent examples, see:

3a Kawamata Y, Vantourout JC, Hickey DP, Bai P, Chen L, Hou Q, Qiao W, Barman K, Edwards MA, Garrido-Castro AF, deGruyter JN, Nakamura H, Knouse K, Qin C, Clay KJ, Bao D, Li C, Starr JT, Garcia-Irizarry C, Sach N, White HS, Neurock M, Minteer SD, Baran PS. J. Am. Chem. Soc. 2019; 141: 6392
3b Zhang X, McNally A. ACS Catal. 2019; 9: 4862
3c Boddy AJ, Affron DP, Cordier CJ, Rivers EL, Spivey AC, Bull JA. Angew. Chem. Int. Ed. 2019; 58: 1458
3d Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
3e Nicolaou KC, Hale CR. H, Nilewski C, Ioannidou HA. Chem. Soc. Rev. 2012; 41: 5185

4a Naidu KM, Suresh A, Subbalakshmi J, Sriram D, Yogeeswari P, Raghavaiah P, Sekhar KV. C. Eur. J. Med. Chem. 2014; 87: 71
4b Sun J, Lin C, Qin X, Dong X, Tu Z, Tang F, Chen C, Zhang J. Bioorg. Med. Chem. Lett. 2015; 25: 3129
4c Perrone MG, Vitale P, Panella A, Fortuna CG, Scilimati A. Eur. J. Med. Chem. 2015; 94: 252

5a Dallanoce C, Magrone P, Matera C, Frigerio F, Grazioso G, DeAmici M, Fucile S, Piccari V, Frydenvang K, Pucci L, Gotti C, Clementi F, DeMicheli C. ChemMedChem 2011; 6: 889
5b Soni A, Rehman A, Naik K, Dastidar S, Alam MS, Ray A, Chaira T, Shah V, Palle VP, Cliffe IA, Sattigeri VJ. Bioorg. Med. Chem. Lett. 2013; 23: 1482
5c Kaur K, Kumar V, Sharma AK, Gupta GK. Eur. J. Med. Chem. 2014; 77: 121

For reviews, see:

6a Paton RM. 1,2,5-Oxadiazoles . In Comprehensive Heterocyclic Chemistry II, Vol. 4. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 229-266
6b Nikonov GN, Bobrov S. 1,2,5-Oxadiazoles . In Comprehensive Heterocyclic Chemistry III, Vol. 5. Katritzky AR, Ramsden CA. V, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008: 316-393
6c Fershtat LL, Makhova NN. Russ. Chem. Rev. 2016; 85: 1097
6d Zlotin SG, Dalinger IL, Makhova NN, Tartakovsky VA. Russ. Chem. Rev. 2020; 89: 1
6e Makhova NN, Belen’kii LI, Gazieva GA, Dalinger IL, Konstantinova LS, Kuznetsov VV, Kravchenko AN, Krayushkin MM, Rakitin OA, Starosotnikov AM, Fershtat LL, Shevelev SA, Shirinian VZ, Yarovenko VN. Russ. Chem. Rev. 2020; 89: 55

7a Zhao J, Li Y, Hunt A, Zhang J, Yao H, Li Z, Zhang J, Huang F, Ade H, Yan H. Adv. Mater. 2016; 28: 1868
7b Cameron J, Abed MM, Chapman SJ, Findlay NJ, Skabara PJ, Horton PN, Coles SJ. J. Mater. Chem. C 2018; 6: 3709

For selected examples, see:

8a Stepanov AI, Astrat’ev AA, Sheremetev AB, Lagutina NK, Palysaeva NV, Tyurin AY, Aleksandrova NS, Sadchikova NP, Suponitsky KYu, Atamanenko OP, Konyushkin LD, Semenov RV, Firgang SI, Kiselyov AS, Semenova MN, Semenov VV. Eur. J. Med. Chem. 2015; 94: 237
8b Pal P, Gandhi HP, Kanhed AM, Patel NR, Mankadia NN, Baldha SN, Barmade MA, Murumkar PR, Yadav MR. Eur. J. Med. Chem. 2017; 130: 107
8c Porta F, Gelain A, Barlocco D, Ferri N, Marchianò S, Cappello V, Basile L, Guccione S, Meneghetti F, Villa S. Chem. Biol. Drug Des. 2017; 90: 820

9 Stokes JM, Yang K, Swanson K, Jin W, Cubillos-Ruiz A, Donghia NM, MacNair CR, French S, Carfrae LA, Bloom-Ackerman Z, Tran VM, Chiappino-Pepe A, Badran AH, Andrews IW, Chory EJ. Church G. M, Brown ED, Jaakkola TS, Barzilay R, Collins JJ. Cell 2020; 180: 688

For selected examples, see:

10a Zhang Q, Shreeve JM. Chem. Rev. 2014; 114: 10527
10b Zhang J, Shreeve JM. J. Am. Chem. Soc. 2014; 136: 4437
10c Palysaeva NV, Gladyshkin AG, Vatsadze IA, Suponitsky KYu, Dmitriev DE, Sheremetev AB. Org. Chem. Front. 2019; 6: 249
10d Wei H, He C, Zhang J, Shreeve JM. Angew. Chem. Int. Ed. 2015; 54: 9367
10e Zhang J, Mitchell LA, Parrish DA, Shreeve JM. J. Am. Chem. Soc. 2015; 137: 10532
10f Fershtat LL, Makhova NN. ChemPlusChem 2020; 85: 13
10g Sun Q, Shen C, Li X, Lin Q, Lu M. J. Mater. Chem. A 2017; 5: 11063
10h He C, Imler GH, Parrish DA, Shreeve JM. J. Mater. Chem. A 2018; 6: 16833

11 Kesornpun C, Aree T, Mahidol C, Ruchirawat S, Kittakoop P. Angew. Chem. Int. Ed. 2016; 55: 3997
12 Larin AA, Fershtat LL, Ananyev IV, Makhova NN. Tetrahedron Lett. 2017; 58: 3993

13a Padwa A, Bur S. Adv. Heterocycl. Chem. 2016; 119: 241
13b Rosenau T, Adelwӧhrer C, Hofinger A, Mereiter K, Kosma P. Eur. J. Org. Chem. 2004; 1323
13c Trogu E, de Sarlo F, Machetti F. Chem. Eur. J. 2009; 15: 7940
13d Maestri G, Caneque T, Della Ca’ N, Derat E, Catellani M, Chiusoli GP, Malacria M. Org. Lett. 2016; 18: 6108

For selected examples, see:

14a Nicolaides DN, Gallos JK. Synthesis 1981; 638
14b Olofson RA, Michelman JS. J. Am. Chem. Soc. 1964; 86: 1863
14c Shaposhnikov SD, Pirogov SV, Mel’nikova SF, Tselinsky IV, Näther C, Graening T, Traulsen T, Friedrichsen W. Tetrahedron 2003; 59: 1059

15 Boulton AJ, Katritzky AR, Majid-Hamid A. J. Chem. Soc. C 1967; 2005

For reviews, see:

16a Ruccia M, Vivona N, Spinelli D. Adv. Heterocycl. Chem. 1981; 29: 141
16b Vivona N, Buscemi S, Frenna V, Cusmano G. Adv. Heterocycl. Chem. 1993; 56: 49

For reviews, see:

17a Boulton AJ, Ghosh PB. Adv. Heterocycl. Chem. 1969; 10: 1
17b Katritzky AR, Gordeev MF. Heterocycles 1993; 35: 483

18 Burakevich JV, Butler RS, Volpp GP. J. Org. Chem. 1972; 37: 593
19 Wieland H. Justus Liebigs Ann. Chem. 1921; 424: 107
20 Bruker. APEX-III . Bruker AXS Inc; Madison (WI, USA): 2018
21 Krause L, Herbst-Irmer R, Sheldrick GM, Stalke D. J. Appl. Crystallogr. 2015; 48: 3
22 Sheldrick GM. Acta Crystallogr., Sect. A 2015; 71: 3
23 Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
24 CCDC 1982203 (3c) and 1982204 (4a) 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.
25 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich A, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 09, Revision D.01 . Gaussian, Inc; Wallingford: 2016
26 Perdew J, Ernzerhof M, Burke K. J. Chem. Phys. 1996; 105: 9982
27 Carlo A, Barone V. J. Chem. Phys. 1999; 110: 6158
28 Grimme S, Ehrlich S, Goerigk L. J. Comput. Chem. 2011; 32: 1456
29 Vivona N, Macaluso G, Frenna V. J. Chem. Soc., Perkin Trans. 1 1983; 483
30 Eaton JK, Ruberto RA, Kramm A, Viswanathan VS, Schreiber SL. J. Am. Chem. Soc. 2019; 141: 20407

Supplementary Material

Supporting Information (PDF)