Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence

Jungang Wang; Yan Cheng; Jiachen Xiang; Anxin Wu

doi:10.1055/s-0037-1612087

Synlett, Table of Contents

Synlett 2019; 30(06): 743-747
DOI: 10.1055/s-0037-1612087

letter

Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I₂/Cu(NO₃)₂•3H₂O-Assisted Domino Sequence

Jungang Wang

^aSchool of Chemical Engineering, Guizhou Minzu University, Guiyang 550025, P. R. of China

,

Yan Cheng

^bKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China Email: chwuax@mail.ccnu.edu.cn

,

Jiachen Xiang

^bKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China Email: chwuax@mail.ccnu.edu.cn

,

Anxin Wu*

^bKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China Email: chwuax@mail.ccnu.edu.cn

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Abstract

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Abstract

A new strategy has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available arylacetylenes and α-amino acids in the presence of Cu(NO₃)₂•3H₂O and iodine. This reaction process involves the I₂/Cu(NO₃)₂•3H₂O-assisted transformation of arylacetylene to α-iodo acetophenone, Kornblum oxidation to phenylglyoxal, condensation to imine, decarboxylation/annulation/oxidation reaction sequence to approach 2,5-disubstituted oxazoles.

Key words

oxazoles - α-amino acids - copper catalysis - cascade reactions - alkynes

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References

References and Notes

1a Kibriz IE, Sacmaci M, Sahin E, Yildirim IP. Tetrahedron 2017; 73: 1795
1b Jin Z. Nat. Prod. Rep. 2011; 28: 1143
1c Wan C, Gao L, Wang Q, Zhang J, Wang Z. Org. Lett. 2010; 12: 3902
1d Davyt D, Serra G. Mar. Drugs 2010; 8: 2755
1e Heng S, Gryncel KR, Kantrowitz ER. Bioorg. Med. Chem. 2009; 17: 3916
1f Zhang J, Ciufolini MA. Org. Lett. 2009; 11: 2389
1g Hughes RA, Moody C. J. Angew. Chem. Int. Ed. 2007; 46: 7930
1h Dalvie DK, Kalgutkar AS, Khojasteh-Bakht SC, Obach RS, O’Donnell JP. Chem. Res. Toxicol. 2002; 15: 269

2 Pettit GR, Knight JC, Delbert L, Davenport R, Pettit RK, Tucker BE, Schmidt JM. J. Nat. Prod. 2002; 65: 1793
3 Coqueron P.-Y, Didier C, Ciufolini MA. Angew. Chem. Int. Ed. 2003; 42: 1411
4 Raju R, Gromyko O, Fedorenko V, Luzhetskyy A, Müller R. Tetrahedron Lett. 2012; 53: 3009
5 Momose Y, Maekawa T, Yamano T, Kawada M, Odaka H, Ikeda H, Sohda T. J. Med. Chem. 2002; 45: 1518
6 Priestap HA, Barbieri MA, Johnson F. J. Nat. Prod. 2012; 75: 1414
7 Todd PA, Brogden RN. Drugs 1986; 32: 291
8 Hashimoto H, Imamura K, Haruta J.-I, Wakitani K. J. Med. Chem. 2002; 45: 1511

9a Gulevich AV, Dudnik AS, Chernyak N, Gevorgyan V. Chem. Rev. 2013; 113: 3084
9b Gissibl A, Finn MG, Reiser O. Org. Lett. 2005; 7: 2325
9c Atkins JM, Vedejs E. Org. Lett. 2005; 7: 3351

For selected examples, see:

10a Weng Y, Lv W, Yu J, Ge B, Cheng G. Org. Lett. 2018; 20: 1853
10b Hu Y, Yi R, Wang C, Xin X, Wu F, Wan B. J. Org. Chem. 2014; 79: 3052
10c Wang Y.-F, Chen H, Zhu X, Chiba S. J. Am. Chem. Soc. 2012; 134: 11980

For selected examples, see:

11a Zhou R.-R, Cai Q, Li D.-K, Zhuang S.-Y, Wu Y.-D, Wu A.-X. J. Org. Chem. 2017; 82: 6450
11b Xu Z, Zhang C, Jiao N. Angew. Chem. Int. Ed. 2012; 51: 11367
11c Xue W.-J, Li Q, Zhu Y.-P, Wang J.-G, Wu A.-X. Chem. Commun. 2012; 48: 3485

For selected examples, see:

12a Zhang L, Zhao X. Org. Lett. 2015; 17: 184
12b Zheng J, Zhang M, Huang L, Hu X, Wu W, Huang H, Jiang H. Chem. Commun. 2014; 50: 3609
12c Odabachian Y, Tong S, Wang Q, Wang M, Zhu J. Angew. Chem. Int. Ed. 2013; 52: 10878

For selected examples, see:

13a Li X, Li C, Yin B, Liu P, Li J, Shi Z, Li C. Chem. Asian J. 2013; 8: 1408
13b Wang Y, Li Z, Huang Y, Tang C, Wu X, Xu J, Yao H. Tetrahedron 2011; 67: 7406
13c Huang Y, Ni L, Gan F, He Y, Xu J, Wu X, Yao H. Tetrahedron 2011; 67: 2066

14a Zhang ML, Zhang SH, Liu MC, Cheng J. Chem. Commun. 2011; 47: 11522
14b Shen X.-B, Zhang Y, Chen W.-X, Xiao Z.-K, Hu T.-T, Shao L.-X. Org. Lett. 2014; 16: 1984

15a Saito A, Taniguchi A, Kambara Y, Hanzawa Y. Org. Lett. 2013; 15: 2672
15b Selvi T, Srinivasan K. Chem. Commun. 2014; 50: 10845
15c Wang B, Chen Y, Zhou L, Wang J, Tung C.-H, Xu Z. J. Org. Chem. 2015; 80: 12718
15d Zeng T.-T, Xuan J, Ding W, Wang K, Lu L.-Q, Xiao W.-J. Org. Lett. 2015; 17: 4070
15e Chatterjee T, Cho JY, Cho EJ. J. Org. Chem. 2016; 81: 6995

16 Pan J, Li X, Qiu X, Luo X, Jiao N. Org. Lett. 2018; 20: 276

17a Han X. -L, Zhou C.-J, Liu X.-G, Zhang S.-S, Wang H, Li Q. Org. Lett. 2017; 19: 6108
17b Querard P, Girard SA, Uhlig N, Li C.-J. Chem. Sci. 2015; 6: 7332
17c Wachenfeldt HV, Röse P, Paulsen F, Loganathan N, Strand D. Chem. Eur. J. 2013; 19: 7982
17d Davies PW, Cremonesi A, Dumitrescu L. Angew. Chem. Int. Ed. 2011; 50: 8931
17e Bartoli G, Cimarelli C, Cipolletti R, Diomedi S, Giovannini R, Mari M, Marsili L, Marcantoni E. Eur. J. Org. Chem. 2012; 630

18a Yagyu T, Takemoto Y, Yoshimura A, Zhdankin VV, Saito A. Org. Lett. 2017; 19: 2506
18b Mallick R, Prabagar KB, Sahoo AK. J. Org. Chem. 2017; 82: 10583
18c Yang W, Zhang R, Yi F, Cai M. J. Org. Chem. 2017; 82: 5204
18d Rassadin VA, Boyarskiy VP, Kukushkin VY. Org. Lett. 2015; 17: 3502
18e He W, Li C, Zhang L. J. Am. Chem. Soc. 2011; 133: 8482
18f Li X, Huang L, Chen H, Wu W, Huang H, Jiang H. Chem. Sci. 2012; 3: 3463

19 Cano I, Álvarez E, Nicasio MC. J, Pérez P. J. Am. Chem. Soc. 2011; 133: 191

20a Ma JW, Wang Q, Wang XG, Liang YM. J. Org. Chem. 2018; 83: 13296
20b Suzuki S, Saito A. J. Org. Chem. 2017; 82: 11859
20c Asari N, Takemoto Y, Shinomoto Y, Yagyu T, Yoshimura A, Zhdankin VV, Saito A. Asian J. Org. Chem. 2016; 5: 1314
20d Bay S, Baumeister T, Hashmi AS. K, Röder T. Org. Process Res. Dev. 2016; 20: 1297
20e Sueda T, Kawada A, Urashi Y, Teno N. Org. Lett. 2013; 15: 1560
20f Hashmi AS. K, Jaimes MC. B, Schuster AM, Rominger F. J. Org. Chem. 2012; 77: 6394
20g Senadi GC, Hu W, Hsiao J.-S, Vandavasi JK, Chen C.-Y, Wang J. Org. Lett. 2012; 14: 4478
20h Hashmi AS. K, Weyrauch JP, Schuster A, Hengst T, Schetter A, Littmann A, Rudolph M, Hamzic M, Visus J, Rominger F, Frey W, Bats JW. Chem. Eur. J. 2010; 16: 956

21a Humphrey JM, Chamberlin AR. Chem. Rev. 1997; 97: 2243
21b Schönberg A, Moubasher R. Chem. Rev. 1952; 50: 261
21c Domling A, Beck B, Eichelberger U, Sakamuri S, Menon S, Chen QZ, Lu YC, Wessjohann LA. Angew. Chem. Int. Ed. 2006; 45: 7235
21d Bartoccini F, Casoli M, Mari M, Piersanti G. J. Org. Chem. 2014; 79: 3255
21e Wang HQ, Xu WT, Xin LL, Liu WM, Wang ZQ, Xu K. J. Org. Chem. 2016; 81: 3681
21f Xiang JC, Cheng Y, Wang ZX, Ma JT, Wang M, Tang BC, Wu YD, Wu AX. Org. Lett. 2017; 19: 2997
21g Xu W, Fu H. J. Org. Chem. 2011; 76: 3846

22a Yan YZ, Wang ZY. Chem. Commun. 2011; 9513
22b Xu W, Fu H. J. Org. Chem. 2011; 76: 3846
22c Bi H.-P, Zhao L, Liang Y.-M, Li C.-J. Angew. Chem. Int. Ed. 2009; 48: 792
22d Zhang C, Das D, Seidel D. Chem. Sci. 2011; 2: 233

23a Xu W, Kloeckner U, Nachtsheim BJ. J. Org. Chem. 2013; 78: 6065
23b Hu T, Yan H, Liu X, Wu C, Fan Y, Huang J, Huang G. Synlett 2015; 26: 2866
23c Xiang JC, Wang JG, Wang M, Meng XG, Wu A. Tetrahedron 2014; 70: 7470
23d Zhu YP, Lian M, Jia FC, Liu MC, Yuan JJ, Gao QH, Wu AX. Chem. Commun. 2012; 48: 9086
23e Wu X, Gao QH, Liu S, Wu AX. Org. Lett. 2014; 16: 2888

24a Viswanadham KK. D R, Reddy MP, Sathyanarayana P, Ravi O, Kantc R, Reddy SB. Chem. Commun. 2014; 50: 13517
24b Kalmode HP, Vadagaonkar KS, Chaskar AC. Synthesis 2015; 47: 429
24c Kalmode HP, Vadagaonkar KS, Chaskar AC. RSC Adv. 2014; 4: 60316

25a Wan JP, Zhou Y, Liu Y, Sheng S. Green Chem. 2016; 18: 402
25b Cao S, Liu Y, Hu C, Wen C, Wan JP. ChemCatChem 2018; 10: 5021

26 General procedure for synthesis of 3 (3ac as an example) The mixture of phenylacetylene 1a (1.0 mmol), 2-amino-4-methylpentanoic 2c (1.0 mmol) was mixed with Cu(NO₃)₂•3H₂O (0.5 mmol), and I₂ (1.0 mmol). The mixture was heated at 60 °C in 4 mL of DMSO in a sealed vessel for 5 h till almost completed conversion of the substrates monitored by TLC analysis. Then 50 mL water was added to the mixture, which was extracted with EtOAc three times (3 × 50 mL). The extract was washed with Na₂S₂O₃ solution, dried over anhydrous Na₂SO₄ then the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/EtOAc = 50/1) to afford the product 3ac” here

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