Synthesis of 2-Aryl-3-(arylselanyl)imidazo[1,2-a]pyridines: Copper­-Catalyzed One-Pot, Two-Step Se-Arylation of Selenium with Imidazopyridines and Triarylbismuthanes

Kaito Kondo; Mio Matsumura; Keiko Kanasaki; Yuki Murata; Naoki Kakusawa; Shuji Yasuike

doi:10.1055/s-0036-1591972

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(11): 2200-2210
DOI: 10.1055/s-0036-1591972

paper

Synthesis of 2-Aryl-3-(arylselanyl)imidazo[1,2-a]pyridines: Copper-Catalyzed One-Pot, Two-Step Se-Arylation of Selenium with Imidazopyridines and Triarylbismuthanes

Kaito Kondo

^aSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, Japan eMail: m-matsu@dpc.agu.ac.jp eMail: s-yasuik@dpc.agu.ac.jp

,

Mio Matsumura*

^aSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, Japan eMail: m-matsu@dpc.agu.ac.jp eMail: s-yasuik@dpc.agu.ac.jp

,

Keiko Kanasaki

^aSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, Japan eMail: m-matsu@dpc.agu.ac.jp eMail: s-yasuik@dpc.agu.ac.jp

,

Yuki Murata

^aSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, Japan eMail: m-matsu@dpc.agu.ac.jp eMail: s-yasuik@dpc.agu.ac.jp

,

Naoki Kakusawa

^bFaculty of Pharmaceutical Sciences, Hokuriku University, Ho-3 Kanagawa-machi, Kanazsawa 920-1181, Japan

,

Shuji Yasuike*

^aSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, Japan eMail: m-matsu@dpc.agu.ac.jp eMail: s-yasuik@dpc.agu.ac.jp

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Abstract

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Abstract

A simple and general method for the synthesis of 2-aryl-3-(arylselanyl)imidazo[1,2-a]pyridines is described. A one-pot, two-step reaction between triarylbismuthanes and diimidazopyridyl diselenides, generated from imidazo[1,2-a]pyridines and Se powder in the presence of CuI and 1,10-phenanthroline, affords 3-selanylimidazopyridines in moderate to excellent yields under aerobic conditions. The reactions proceed efficiently and the selenium and all the aryl groups on bismuth are transferred to the coupling products. Triarylbismuthanes give better results compared to other aryl donors containing elements such as boron, silicon, tin, and iodine.

Key words

imidazo[1,2-a]pyridines - selenium - triarylbismuthanes - copper catalyst - one-pot, two-step reaction

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Referenzen

References

1a Wirth T. Organoselenium Chemistry . Wiley-VCH; Weinheim: 2012
1b Ogawa A. In Main Group Metals in Organic Synthesis . Vol. 2. Yamamoto H. Oshima K. Chap. 15 Wiley-VCH; Weinheim: 2004: 813
1c Santoro S. Azeredo JB. Nascimento V. Sancineto L. Brage AL. Santi C. RSC Adv. 2014; 4: 31521
1d Manjare ST. Kim Y. Churchill DG. Acc. Chem. Res. 2014; 47: 2985
1e Marini F. Sternativo S. Synlett 2013; 24: 11
1f Mukherjee AJ. Zade SS. Singh H.-B. Sunoj RB. Chem. Rev. 2010; 110: 4357
1g Freudendahl DM. Shahzad SA. Wirth T. Eur. J. Org. Chem. 2009; 1649

2a Nogueira CW. Rocha JB. T. Arch. Toxicol. 2011; 85: 1313
2b Sarma BK. Mugesh G. Org. Biomol. Chem. 2008; 6: 965
2c Nogueira CW. Zeni G. Rocha JB. T. Chem. Rev. 2004; 104: 6255
2d Mugesh G. Mont WW. Sies H. Chem. Rev. 2001; 101: 2125

3a Ranu BC. Dey R. Chatterjee T. Ahammed S. ChemSusChem 2012; 5: 22
3b Beletskaya IP. Ananikov VP. Chem. Rev. 2011; 111: 1596
3c Beletskaya IP. Ananikov VP. In Catalyzed Carbon-Heteroatom Bond Formation . Yudin AK. Wiley-VCH; Weinheim: 2011. Chap. 3, 69
3d Qiao JX. Lam PY. S. Synthesis 2011; 829
3e Beletskaya IP. Ananikov VP. Eur. J. Org. Chem. 2007; 3431

4a Li Z. Hong J. Zhou X. Tetrahedron 2011; 67: 3690
4b Shibahara F. Kanai T. Yamaguchi E. Kamei A. Yamauchi T. Murai T. Chem. Asian J. 2014; 9: 237

5a Rosario AR. Casola KK. Oliveira CE. S. Zeni G. Adv. Synth. Catal. 2013; 355: 2960
5b Gandeepan P. Mo J. Ackermann L. Chem. Commun. 2017; 53: 5906

6 Gao C. Wu G. Min L. Liu M. Gao W. Ding J. Chen J. Huang X. Wu H. J. Org. Chem. 2017; 82: 250
7 Luo D. Wu G. Yang H. Liu M. Gao W. Huang X. Chen J. Wu H. J. Org. Chem. 2016; 81: 4485
8 Cera G. Ackermann L. Chem. Eur. J. 2016; 22: 8475

9a Enguehard-Gueiffier C. Gueiffer A. Mini Rev. Med. Chem. 2007; 7, 888
9b Goel R. Luxami V. Paul K. Curr. Top. Med. Chem. 2016; 16: 3590

10 Wan J. Zheng C.-J. Fung M.-K. Liu X.-K. Lee C.-S. Zhang X.-H. J. Mater. Chem. 2012; 22: 4502

11a Katsura Y. Nishino S. Takasugi H. Chem. Pharm. Bull. 1991; 39: 2937
11b Abe Y. Kayakiri H. Satoh S. Inoue T. Sawada Y. Inamura N. Asano M. Aramori I. Hatori C. Sawai H. Oku T. Tanaka H. J. Med. Chem. 1998; 41: 4587
11c Jain AN. J. Med. Chem. 2004; 47: 947
11d Hanson SM. Morlock EV. Satyshur KA. Czajkowski C. J. Med. Chem. 2008; 51: 7243
11e Boggs S. Elitzin VI. Gudmundsson K. Martin MT. Sharp MJ. Org. Process Res. Dev. 2009; 13: 781
11f Linton A. Kang P. Ornelas M. Kephart S. Hu Q. Pairish M. Jiang Y. Guo C. J. Med. Chem. 2011; 54: 7705

12 Vieira BM. Thurow S. da Costa M. Casaril AM. Domingues M. Schumacher RF. Perin G. Alves D. Savegnago L. Lenardão EJ. Asian J. Org. Chem. 2017; 6: 1635
13 Gao Z. Zhu X. Zhang R. RSC Adv. 2014; 4: 19891
14 Ji X.-M. Zhou S.-J. Chen F. Zhang X.-G. Tang R.-Y. Synthesis 2015; 47: 659
15 Rafique J. Saba S. Rosário AR. Braga AL. Chem. Eur J. 2016; 22: 11854
16 Jana S. Chakraborty A. Mondal S. Hajra A. RSC Adv. 2015; 5: 77534
17 Ge W. Zhu X. Wei Y. Eur. J. Org. Chem. 2013; 6015

18a Gagnon A. Dansereau J. Le Roch A. Synthesis 2017; 49: 1707
18b Condon S. Pichon C. Davi M. Org. Prep. Proced. Int. 2014; 46: 89
18c Ollevier T. Bismuth-Mediated Organic Reactions: Topics in Current Chemistry 311. Springer; Heidelberg: 2012
18d Matano Y. In Main Group Metals in Organic Synthesis . Vol. 2. Yamamoto H. Oshima K. Wiley-VCH; Weinheim: 2004: 753
18e Elliott GI. Konopelski JP. Tetrahedron 2001; 57: 5683

19a Arnauld T. Barton DH. R. Normant J.-F. J. Org. Chem. 1999; 64: 3722
19b Kobiki Y. Kawaguchi S. Ohe T. Ogawa A. Beilstein J. Org. Chem. 2013; 9: 1141

20a Matsumura M. Shibata K. Ozeki S. Yamada M. Murata Y. Kakusawa N. Yasuike S. Synthesis 2016; 48: 730
20b Matsumura M. Kumagai H. Murata Y. Kakusawa N. Yasuike S. J. Organomet. Chem. 2016; 807: 11

21 Matsumura M. Sakata Y. Iwase A. Kawahata M. Kitamura Y. Murata Y. Kakusawa N. Yamaguchi K. Yausike S. Tetrahedron Lett. 2016; 57: 5484
22 Sun P. Jiang M. Wei W. Min Y. Zhang W. Li W. Yang D. Wang H. J. Org. Chem. 2017; 82: 2906
23 Combes S. Finet J.-P. Synth. Commun. 1996; 26: 4569
24 Murafuji T. Nishio K. Nagasue M. Tanabe A. Aono M. Sugihara Y. Synthesis 2000; 1208
25 Arnauld T. Barton DH. R. Normant J.-F. J. Org. Chem. 1999; 64: 3722
26 Matano Y. Kinoshita M. Suzuki H. Bull. Chem. Soc. Jpn. 1992; 65: 3504
27 Petiot P. Gagnon A. Eur. J. Org. Chem. 2013; 5282
28 Chen Z. Cao G. Zhang F. Li H. Xu J. Miao M. Ren H. Synlett 2017; 28: 1795
29 El Kazzouli S. du Bellay AG. Berteina-Raboin S. Delagrange P. Caignard D.-H. Guillaumet G. Eur. J. Med. Chem. 2011; 46: 4252
30 McDonald IM. Peese KM. Org. Lett. 2015; 17: 6002
31 Yu J. Jin Y. Zhang H. Yang X. Fu H. Chem. Eur. J. 2013; 19: 16804
32 Redon S. Kosso AR. O. Broggi J. Vanelle P. Tetrahedron Lett. 2017; 58: 2771
33 Rafique J. Saba S. Rosário AR. Braga AL. Chem. Eur. J. 2016; 22: 11854

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Supporting Information

Synthesis of 2-Aryl-3-(arylselanyl)imidazo[1,2-a]pyridines: Copper­-Catalyzed One-Pot, Two-Step Se-Arylation of Selenium with Imidazopyridines and Triarylbismuthanes

Synthesis of 2-Aryl-3-(arylselanyl)imidazo[1,2-a]pyridines: Copper-Catalyzed One-Pot, Two-Step Se-Arylation of Selenium with Imidazopyridines and Triarylbismuthanes