Synthesis of 4-Nitroisoxazoles via NO/NO2-Mediated Heterocyclization of Aryl-Substituted α,β-Unsaturated Ketones

Dmitry A. Vasilenko; Kirill S. Sadovnikov; Kseniya N. Sedenkova; Anastasiya V. Kurova; Yuri K. Grishin; Tamara S. Kuznetsova; Victor B. Rybakov; Yulia A. Volkova; Elena B. Averina

doi:10.1055/s-0039-1690053

Synthesis, Table of Contents

Synthesis 2020; 52(09): 1398-1406
DOI: 10.1055/s-0039-1690053

paper

Synthesis of 4-Nitroisoxazoles via NO/NO₂-Mediated Heterocyclization of Aryl-Substituted α,β-Unsaturated Ketones

Dmitry A. Vasilenko

^aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 bd. 3, Moscow 119991, Russian Federation Email: elaver@med.chem.msu.ru

,

Kirill S. Sadovnikov

^aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 bd. 3, Moscow 119991, Russian Federation Email: elaver@med.chem.msu.ru

,

Kseniya N. Sedenkova

^aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 bd. 3, Moscow 119991, Russian Federation Email: elaver@med.chem.msu.ru

^bInstitute of Physiologically Active Compounds, Severny Proezd 1, Chernogolovka, Moscow Region 142432, Russian Federation

,

Anastasiya V. Kurova

^aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 bd. 3, Moscow 119991, Russian Federation Email: elaver@med.chem.msu.ru

,

Yuri K. Grishin

^aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 bd. 3, Moscow 119991, Russian Federation Email: elaver@med.chem.msu.ru

,

Tamara S. Kuznetsova

^aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 bd. 3, Moscow 119991, Russian Federation Email: elaver@med.chem.msu.ru

,

Victor B. Rybakov

^aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 bd. 3, Moscow 119991, Russian Federation Email: elaver@med.chem.msu.ru

,

Yulia A. Volkova

^aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 bd. 3, Moscow 119991, Russian Federation Email: elaver@med.chem.msu.ru

^cN.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prospect, 47, Moscow 119991, Russian Federation

,

Elena B. Averina∗

^aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 bd. 3, Moscow 119991, Russian Federation Email: elaver@med.chem.msu.ru

^bInstitute of Physiologically Active Compounds, Severny Proezd 1, Chernogolovka, Moscow Region 142432, Russian Federation

› Author Affiliations

Abstract

All articles of this category

Abstract

A straightforward approach for the synthesis of 4-nitroisoxazoles has been developed via heterocyclization of aryl/hetaryl-substituted α,β-unsaturated ketones upon treatment with tetranitromethane-triethylamine (TNM-TEA) complex or t-BuONO. This strategy features high efficiency and wide substrate tolerance under simple reaction conditions.

Key words

4-nitroisoxazoles - alkenes - ketones - heterocycles - ring closure - tert-butyl nitrite - heterocyclization - tetranitromethane

Full Text

References

References

For reviews and some recent examples, see:

1a Cordero FM, Giomi D, Lascialfari L. In Progress in Heterocyclic Chemistry, Vol. 27. Gribble G, Joule J. Elsevier; Amsterdam: 2015: 321
1b Hamama WS, Ibrahim ME, Zoorob HH. Synth. Commun. 2013; 43: 2393
1c Fuse S, Morita T, Nakamura H. Synthesis 2017; 49: 2351
1d Morita T, Yugandar S, Fuse S, Nakamura H. Tetrahedron Lett. 2018; 59: 1159
1e Hu F, Szostaka M. Adv. Synth. Catal. 2015; 357: 2583
1f Galenko AV, Khlebnikov AF, Novikov MS, Pakalnis VV, Rostovskii NV. Russ. Chem. Rev. 2015; 84; 335; Usp. Khim. 2015, 84, 335
1g Dighe SU, Mukhopadhyay S, Kolle S, Kanojiya S, Batra S. Angew. Chem. Int. Ed. 2015; 54: 10926
1h Fu M, Li H, Su M, Cao Z, Liu Y, Liu Q, Guo C. Adv. Synth. Catal. 2019; 361: 3420

2a Barmade MA, Murumkar PR, Sharma MK, Yadav MR. Curr. Top. Med. Chem. 2016; 16: 2863
2b Uto Y. Curr. Pharm. Des. 2016; 22: 3201
2c Sysak A, Obmińska-Mrukowicz B. Eur. J. Med. Chem. 2017; 137: 292
2d Zhu J, Mo J, Lin HZ, Chen Y, Sun HP. Bioorg. Med. Chem. 2018; 23: 3065

3a Doi Y, Chambers HF. In Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases, 8th ed., Vol. 1. Bennett JE, Dolin R, Blaser MJ. Elsevier Saunders; Philadelphia: 2015: 263
3b Farrington M. In Clinical Pharmacology, 11th ed. Bennett PN, Brown MJ, Sharma P. Elsevier Ltd; Churchill Livingstone: 2012: 173

4 Leppik IE. Seizure 2004; 13S1: S5
5 Leucht S, Cipriani A, Spineli L, Mavridis D, Örey D, Richter F, Samara M, Barbui C, Engel RR, Geddes JR, Kissling W, Stapf MP, Lässig B, Salanti G, Davis JM. Lancet 2013; 382: 951
6 Larsen JK, Rafaelsen OJ. Acta Psych. Scand. 1980; 62: 456
7 Liu Y.-Y, Hsiao H.-T, Wang JC.-F, Liu Y.-C, Wu S.-N. Eur. J. Pharm. 2019; 844: 95
8 Sanders S, Harisdangkul V. Am. J. Med. Sci. 2002; 323: 190

9a Zimecki M, Bąchor U, Mączyński M. Molecules 2018; 23: 2724
9b Averina EB, Vasilenko DA, Gracheva YA, Grishin YK, Radchenko EV, Burmistrov VV, Butov GM, Neganova ME, Serkova TP, Redkozubova OM, Shevtsova EF, Milaeva ER, Kuznetsova TS, Zefirov NS. Bioorg. Med. Chem. 2016; 24: 712

10 Jensen AA, Plath N, Pedersen MH. F, Isberg V, Krall J, Wellendorph P, Stensbol TB, Gloriam DE, Krogsgaard-Larsen P, Frølund B. J. Med. Chem. 2013; 56: 1211

11a Drysdale MJ, Dymock BW, Finch H, Webb P, Mcdonald E, James KE, Cheung KM, Mathews TP. WO2004072051 A1, 2004 ; Chem. Abstr. 2004, 141, 696360
11b Vasilenko DA, Averina EB, Zefirov NA, Wobith B, Grishin YK, Rybakov VB, Zefirova ON, Kuznetsova TS, Kuznetsov SA, Zefirov NS. Mendeleev Commun. 2017; 27: 228

12 Vasilenko DA, Dueva EV, Kozlovskaya LI, Zefirov NA, Grishin YK, Butov GM, Palyulin VA, Kuznetsova TS, Karganova GG, Zefirova ON, Osolodkin DI, Averina EB. Bioorg. Chem. 2019; 87: 629
13 Madsen U, Bang-Andersen B, Brehm L, Christensen IT, Ebert B, Kristoffersen IT. S, Lang Y, Krogsgaard-Larsen P. J. Med. Chem. 1996; 39: 1682
14 Jorgensen AT, Tagmose L, Stensbol TB, Vestergaard HT, Engblom C, Kristiansen U, Sanchez C, Krogsgaard-Larsen P, Liljefors T. J. Med. Chem. 2002; 45: 2454
15 Simoni D, Rondanin R, Baruchello R, Rizzi M, Grisolia G, Eleopra M, Grimaudo S, Di Cristina A, Pipitone MR, Bon-giorno MR, Arico M, Invidiata FP, Tolomeo M. J. Med. Chem. 2008; 51: 4796
16 Srinivas A, Nagaraj A, Reddy CS. J. Heterocycl. Chem. 2009; 46: 497

17a The Nitro Group in Organic Synthesis . Ono N. Wiley-VCH; New York: 2001: 372
17b Denmark SE, Cottell JJ. In The Chemistry of Heterocyclic Compounds, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Vol. 59. Padwa A, Pearson WH. Wiley; New York: 2002: 83
17c Ioffe SL. In Nitrile Oxide, Nitrones and Nitronates in Organic Synthesis, 2nd ed. Feuer H. Wiley-VCH; Weinheim: 2008: 435
17d Halimehjani AZ, Namboothiri IN. N, Hooshmand SE. RSC Adv. 2014; 4: 48022

18a Zhang Y, Wei B, Lin H, Cui W, Zeng X, Fan X. Adv. Synth. Catal. 2015; 357: 1299
18b Xia X, Zhu Q, Wang J, Chen J, Cao W, Zhu B, Wu X. J. Org. Chem. 2018; 83: 14617
18c Zhu B, Lee R, Yin Y, Li F, Coote ML, Jiang Z. Org. Lett. 2018; 20: 429
18d Zhu B, Li F, Lu B, Chang J, Jiang Z. J. Org. Chem. 2018; 83: 11350

19 Adamo MF. A, Nagabelli M. Org. Lett. 2008; 10: 1807
20 Rajanarendar E, Reddy MN, Reddy KG, Krishna SR. Tetrahedron Lett. 2012; 53: 2909

21a Reddy MS, Chowhan LR, Kumar NS, Ramesh P, Mukkamala SB. Tetrahedron Lett. 2018; 59: 1366
21b Reddy MS, Kumar NS, Chowhan LR. RSC Adv. 2018; 8: 35587
21c Liu K, Xiong Y, Wang Z.-F, Tao H.-Y, Wang C.-J. Chem. Commun. 2016; 52: 9458

22a Nagaraju S, Satyanarayana N, Paplal B, Vasu AK, Kanvah S, Sridhar B, Sripadi P, Kashinath D. RSC Adv. 2015; 5: 94474
22b Zhang J, Liu X, Ma X, Wang R. Chem. Commun. 2013; 49: 9329
22c Baschieri A, Bernardi L, Ricci A, Suresh S, Adamo MF. A. Angew. Chem. Int. Ed. 2009; 48: 9342
22d Disetti P, Moccia M, Illera DS, Suresha S, Adamo MF. A. Org. Biomol. Chem. 2015; 13: 10609
22e Rout S, Joshi H, Singh VK. Org. Lett. 2018; 20: 2199
22f Pei Q.-L, Sun H.-W, Wu Z.-J, Du X.-L, Zhang X.-M, Yuan W.-C. J. Org. Chem. 2011; 76: 7849

23a Chen X.-Y, Liu Q, Chauhan P, Li S, Peuronen A, Rissanen K, Jafari E, Enders D. Angew. Chem. Int. Ed. 2017; 56: 6241
23b Chen X.-Y, Li S, Sheng H, Liu Q, Jafari E, Essen C, Rissanen K, Enders D. Chem. Eur. J. 2017; 23: 13042
23c Liu X.-L, Han W.-Y, Zhang X.-M, Yuan W.-C. Org. Lett. 2013; 15: 1246
23d Chauhan P, Mahajan S, Raabe G, Enders D. Chem. Commun. 2015; 51: 2270
23e Liu X.-L, Wei Q.-D, Zuo X, Xu S.-W, Yao Z, Wang J.-X, Zhou Y. Adv. Synth. Catal. 2019; 361: 2836
23f Suresh A, Baiju TV, Kumar T, Namboothiri IN. N. J. Org. Chem. 2019; 84: 3158

24 Vasilenko DA, Sedenkova KN, Kuznetsova TS, Averina EB. Synthesis 2019; 51: 1516

25a Volkova YA, Averina EB, Grishin YK, Bruheim P, Kuznetsova TS, Zefirov NS. J. Org. Chem. 2010; 75: 3047
25b Averina EB, Volkova YA, Samoilichenko YV, Grishin YK, Rybakov VB, Kutateladze AG, Elyashberg ME, Kuznetsova TS, Zefirov NS. Tetrahedron Lett. 2012; 53: 1472
25c Averina EB, Vasilenko DA, Samoilichenko YV, Grishin YK, Rybakov VB, Kuznetsova TS, Zefirov NS. Synthesis 2014; 46: 1107
25d Volkova YA, Averina EB, Vasilenko DA, Sedenkova KN, Grishin YuK, Bruheim P, Kuznetsova TS, Zefirov NS. J. Org. Chem. 2019; 84: 3192

For recent examples of various bioactive bis(heterocycles), see:

26a Drapier T, Geubelle P, Bouckaert C, Nielsen L, Laulumaa S, Goffin E, Dilly S, Francotte P, Hanson J, Pochet L, Kastrup JS, Pirotte B. J. Med. Chem. 2018; 61: 5279
26b Venkatraj M, Salado IG, Heeres J, Joossens J, Lewi PJ, Caljon G, Maes L, Veken P, Augustyns K. Eur. J. Med. Chem. 2018; 143: 306
26c Dai H, Ge S, Guo J, Chen S, Huang M, Yang J, Sun S, Ling Y, Shi Y. Eur. J. Med. Chem. 2018; 143: 1066

27a Altukhov KV, Perekalin VV. Usp. Khim. 1976; 45: 2050 ; Chem. Abstr. 1977, 86, 71774s
27b Nielsen AT. Nitrocarbons. Wiley-VCH; Weinheim: 1995: 190
27c Nazin GM, Manelis GB. Russ. Chem. Rev. 1994; 63: 313

28 Khisamutdinov GK, Lyapin NM, Nikitin VG, Slovetskii VI, Fainzil’berg AA. Russ. Chem. Bull. 2009; 58: 2178

For review and recent examples, see:

29a Li P, Jia X. Synthesis 2018; 50: 711
29b He Y, Feng T, Fan X. Org. Lett. 2019; 21: 3918
29c Dai P, Tan X, Luo Q, Yu X, Zhang S, Liu F, Zhang W.-H. Org. Lett. 2019; 21: 5096
29d Sau P, Rakshit A, Alam T, Srivastava KH, Patel BK. Org. Lett. 2019; 21: 4966

30 Hauff J.-P, Tuaillon J, Perrot R. Helv. Chim. Acta 1978; 61: 1207
31 Li L, Zhao M.-N, Ren Z.-H, Li J.-L, Guan Z.-H. Org. Lett. 2012; 14: 3506
32 Cheng Y.-F, Dong X.-Y, Gu Q.-S, Yu Z.-L, Liu X.-Y. Angew. Chem. Int. Ed. 2017; 56: 8883
33 Kesten SJ, Degnan MJ, Hung J, McNamara DJ, Ortwine DF, Uhlendorf SE, Werbel LM. J. Med. Chem. 1992; 35: 3429
34 Canela M.-D, Pérez-Pérez M.-J, Noppen S, Sáez-Calvo G, Díaz JF, Camarasa M.-J, Liekens S, Priego E.-M. J. Med. Chem. 2014; 57: 3924
35 Adeva M, Sahagún H, Caballero E, Clairac RP.-L, Medarde M, Tomé F. J. Org. Chem. 2000; 65: 3387
36 Louie T, Goodman D, Holloway GA, McFadden GI, Mollard V, Watson KG. Bioorg. Med. Chem. Lett. 2010; 20: 4611
37 Shih J.-L, Nguyen TS, May JA. Angew. Chem. Int. Ed. 2015; 54: 9931
38 Zhang S.-L, Denga Z.-Q. Org. Biomol. Chem. 2016; 14: 7282
39 Pesciaioli F, Vincentiis F, Galzerano P, Bencivenni G, Bartoli G, Mazzanti A, Melchiorre P. Angew. Chem. Int. Ed. 2008; 47: 8703
40 Wei H, Li Y, Xiao K, Cheng B, Wang H, Hu L, Zhai H. Org. Lett. 2015; 17: 5974
41 Le PQ, Nguyen TS, May JA. Org. Lett. 2012; 14: 6104
42 Sawada M, Kubo S, Matsumura K, Takemoto Y, Kobayashi H, Tashiro E, Kitahara T, Watanabe H, Imoto M. Bioorg. Med. Chem. Lett. 2011; 21: 1385
43 Chang M.-Y, Chen Y.-C, Chan C.-K. Tetrahedron 2014; 70: 2257
44 Kellogg RM, Nieuwenhuijzen JW, Pouwer K, Vries TR, Broxterman QB, Grimbergen RF. P, Kaptein B, Crois RM. L, de Wever E, Zwaagstra K, van der Laan AC. Synthesis 2003; 1626
45 Lawrence NJ, Armitage ES. M, Greedy B, Cook D, Ducki S, McGown AT. Tetrahedron Lett. 2006; 47: 1637
46 Applequist DE, Gdanski RD. J. Org. Chem. 1981; 46: 2502
47 Duranti E, Balsamini C, Spadoni G, Staccioli L. J. Org. Chem. 1988; 53: 2870
48 Quilico A, Fusco R, Rosnati V. Gazz. Chim. Ital. 1946; 76: 30 ; Chem. Abstr. 1947, 41, 2157

Supplementary Material

Supporting Information

Primary Data

Primary Data