An Intramolecular Cycloaddition Approach to Construct Polysubstituted Pyrrolidones from Alkynyl Carboxamides and PTSA

Xiao-Dan Han; Chuan-Qing Ren; Jian-Ping Fu; Wei Xiong; Hui-Bin Wang; Xiao-Na Dong; Jian-Wei Ji; Ju-Wu Hu

doi:10.1055/s-0036-1588500

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(20): 4703-4710
DOI: 10.1055/s-0036-1588500

paper

An Intramolecular Cycloaddition Approach to Construct Polysubstituted Pyrrolidones from Alkynyl Carboxamides and PTSA

Xiao-Dan Han

^aDepartment of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China

,

Chuan-Qing Ren

^bShaanxi Key Laboratory of Catalysis, School of Chemical & Environmental Science, Shaanxi, Sci-Tech University, Hanzhong, 723000 Shaanxi, P. R. of China eMail: kanxl433@nenu.edu.cn eMail: hjw19771985@163.com

,

Jian-Ping Fu

^aDepartment of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China

,

Wei Xiong

^aDepartment of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China

,

Hui-Bin Wang

^aDepartment of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China

,

Xiao-Na Dong

^aDepartment of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China

,

Jian-Wei Ji

^bShaanxi Key Laboratory of Catalysis, School of Chemical & Environmental Science, Shaanxi, Sci-Tech University, Hanzhong, 723000 Shaanxi, P. R. of China eMail: kanxl433@nenu.edu.cn eMail: hjw19771985@163.com

,

Ju-Wu Hu *

^aDepartment of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

An efficient synthetic route to highly substituted pyrrolidone derivatives has been developed from an easily available alkynyl carboxamide and 4-methylbenzenesulfonic acid (PTSA). In the reaction, PTSA is not only used as acid catalyst but also as a reactant to provide a source for OTs group. A mechanism is proposed to involve the protonation of the alcohol substrate/cyclopropylcarbinol-homoallylic rearrangement/intramolecular N-nucleophilic cyclization reactions.

Keywords

pyrrolidones - alkynyl carboxamides - PTSA - intramolecular cyclization - ring opening

Volltext

Referenzen

References

1a Bhat C. Tilve SG. Tetrahedron Lett. 2013; 54: 245
1b Duan XJ. Li XM. Wang BG. J. Nat. Prod. 2007; 70: 1210
1c Takahashi K. Midori M. Kawano K. Ishihara J. Hatakeyama S. Angew. Chem. Int. Ed. 2008; 47: 6244

2a Armanino N. Carreira EM. J. Am. Chem. Soc. 2013; 135: 6814
2b Yasui Y. Kamisaki H. Takemoto Y. Org. Lett. 2008; 10: 3303
2c Touchy AS. Hakim Siddiki SM. A. Kon K. Shimizu K. ACS Catal. 2014; 4: 3045
2d Carroll FI. Blough BE. Abraham P. Mills AC. Holleman JA. Wolckenhauer SA. Decker AM. Landavazo AK. McElroy T. Navarro HA. Gatch MB. Forster MJ. J. Med. Chem. 2009; 52: 6768

3a Bencini M. Ranucci E. Ferruti P. Manfredi A. Macromol. Rapid Commun. 2006; 27: 1060
3b Heyns IM. Pfukwa R. Klumperman B. Biomacromolecules 2016; 17: 1795
3c Connal LA. Kinnane CR. Zelikin AN. Caruso F. Chem. Mater. 2009; 21: 576

4a Donohue SR. Krushinski JH. Pike VW. Chernet E. Phebus L. Chesterfield AK. Felder CC. Halldin C. Schaus JM. J. Med. Chem. 2008; 51: 5833
4b Kulig K. Sapa J. Nowaczyk A. Filipek B. Malawska B. Eur. J. Med. Chem. 2009; 44: 3994
4c Enz A. Feuerbach D. Frederiksen MU. Gentsch C. Hurth K. Müller W. Nozulak J. Roy BL. Bioorg. Med. Chem. Lett. 2009; 19: 1287
4d Jang DS. Lee GY. Lee YM. Kim YS. Sun H. Kim D. Kim JS. Chem. Pharm. Bull. 2009; 57: 397
4e Myers MC. Wang J.-L. Iera JA. Bang J.-K. Hara T. Saito S. Zambetti GP. Appella DH. J. Am. Chem. Soc. 2005; 127: 6152

5a Castelhano AL. Krantz A. J. Am. Chem. Soc. 1987; 109: 3491
5b Banziger M. Mc Garrity JF. Meul T. J. Org. Chem. 1993; 58: 4010
5c Huang PQ. Wang SL. Ye JL. Ruan YP. Huang YQ. Zheng H. Gao JX. Tetrahedron 1998; 54: 12547
5d Gheorghe A. Schulte M. Reiser O. J. Org. Chem. 2006; 71: 2173
5e Crucianelli E. Martelli G. Orena M. Rinaldi S. Sgolastra F. Tetrahedron: Asymmetry 2009; 20: 1824

6a Blay G. Cardona L. Garcia B. Garcia CL. Pedro JR. Tetrahedron Lett. 1997; 38: 8257
6b Wang PL. Li Y. Wu Y. Li C. Lan Q. Wang XS. Org. Lett. 2015; 17: 3698
6c Haase C. Langer P. Tetrahedron 2009; 65: 4530
6d Mariella P. Fabrizio R. Accorsia L. Parsons A. Ghelﬁ F. Tetrahedron 2010; 66: 1357
6e Gupton J. Nakul T. Bannera E. Kluballa EJ. Halla KE. Tetrahedron 2010; 66: 9113
6f Loke I. Park N. Kempf K. Jagusch C. Schobert R. Laschat S. Tetrahedron 2012; 68: 697
6g Adib M. Mahdavi M. Noghani MA. Bijanzadeh HR. Tetrahedron Lett. 2007; 48: 8056

7a Miyabe H. Asada R. Toyoda A. Takemoto Y. Angew. Chem. Int. Ed. 2006; 45: 5863
7b Ishibashi H. Haruki S. Uchiyama M. Tamura O. Matsuo J. Tetrahedron Lett. 2006; 47: 6263

8a Qi XT. Zhang H. Shao AL. Zhu L. Xu T. Gao M. Liu C. Lan Y. ACS Catal. 2015; 5: 6640
8b Li JQ. Liao RZ. Ding WJ. Cheng Y. J. Org. Chem. 2007; 72: 6266
8c McLaughlin M. Takahashi M. Micalizio GC. Angew. Chem. Int. Ed. 2007; 46: 3912
8d Heinz LJ. Lunn WH. W. Murff RE. Paschal JW. Spangle LA. J. Org. Chem. 1996; 61: 4838

9a Ghorai MK. Tiwari DP. J. Org. Chem. 2010; 75: 6173
9b Dekeukeleire S. D’hooghe M. De Kimpe N. J. Org. Chem. 2009; 74: 1644

10a Yang Q. Lai YY. Xiao WJ. Alper H. Tetrahedron Lett. 2008; 49: 7334
10b Ma SM. Ni BK. Org. Lett. 2002; 4: 639
10c Giambastiani G. Pacini B. Porcelloni M. Poli G. J. Org. Chem. 1998; 63: 804
10d Nedolya NA. Schlyakhtina NI. Valentina PZ. Tetrahedron Lett. 2002; 43: 1569

11 Wei ZY. Knaus EE. Tetrahedron Lett. 1993; 34: 4439

12a McGrane PL. Jensen M. Livinghouse T. J. Am. Chem. Soc. 1992; 114: 5459
12b Gagné MR. Nolan SP. Marks TJ. Organometallics 1990; 9: 1716
12c Gagné MR. Brard L. Conticello VP. Giardelo MA. Stern CL. Marks TJ. Organometallics 1992; 11: 2003
12d Sperger CA. Fiksdahl A. J. Org. Chem. 2010; 75: 4542
12e Doan HD. Goré J. Vatèle JM. Tetrahedron Lett. 1999; 40: 6765
12f Luo FT. Wang RT. Tetrahedron Lett. 1992; 33: 6835
12g Kel’in AV. Sromek AW. Gevorgyan V. J. Am. Chem. Soc. 2001; 123: 2074
12h Cochran BM. Michael FE. J. Am. Chem. Soc. 2008; 130: 2786

13a Hou JY. Wang DZ. Li F. Yan ZY. Liang YM. Liu YQ. Synth. Commun. 2012; 42: 1070
13b Yoda H. Yamazaki H. Kawauchi M. Takabe K. Tetrahedron: Asymmetry 1995; 6: 2669
13c Magnus NA. Staszak MA. Udodong UE. Wepsiec JP. Org. Process Res. Dev. 2006; 10: 899
13d Binder JT. Kirsch SF. Org. Lett. 2003; 8: 2151
13e Yu J. Shi F. Gong LZ. Acc. Chem. Res. 2011; 44: 1156
13f Ibrahem I. Rios R. Vesely J. Cordova A. Tetrahedron Lett. 2007; 48: 6252

14a Kim SY. Park HB. Cho JH. Yoo KH. Oh CH. Bioorg. Med. Chem. Lett. 2009; 19: 2558
14b Guo Z. Orth P. Wong SC. Lavey BJ. Shi NY. Niu X. Lundell DJ. Madison V. Kozlowski JA. Bioorg. Med. Chem. Lett. 2009; 19: 54

15a Chan PW. H. Mothe SR. J. Org. Chem. 2009; 74: 5887
15b Schlummer B. Hartwig JF. Org. Lett. 2002; 4: 1471
15c Pan YM. Zheng FJ. Lin HX. Zhan ZP. J. Org. Chem. 2009; 74: 3148
15d Arcadi A. Rossi E. Tetrahedron 1998; 54: 15253
15e Uchiyama M. Ozawa H. Takuma K. Matsumoto Y. Yonehara M. Hiroya K. Sakamoto T. Org. Lett. 2008; 73: 177
15f Tovar JD. Swager TM. J. Org. Chem. 1999; 64: 6499

16a Han ZY. Xiao H. Chen XH. Gong LZ. J. Am. Chem. Soc. 2009; 131: 9182
16b Muzart J. Tetrahedron 2008; 64: 5815
16c Tamaru Y. Eur. J. Org. Chem. 2005; 2647
16d Yamamoto Y. Gridnev I. D. Patil NT. Jin TN. Chem. Commun. 2009; 5075
16e Bras JL. Muzart J. Tetrahedron 2007; 63: 7942
16f González-Rodrίguez C. Escalante L. Varela JA. Castedo L. Saà C. Org. Lett. 2009; 11: 1531

17a DePuy CH. Top. Curr. Chem. 1973; 40: 73
17b Yadav VK. Balamurugan R. Org. Lett. 2003; 5: 4281
17c Tanaka M. Ubukata M. Matsuo T. Yasue K. Matsumoto K. Kajimoto Y. Ogo T. Inaba T. Org. Lett. 2007; 9: 3331
17d Pan W. Dong D. Wang K. Zhang J. Wu R. Xiang D. Liu Q. Org. Lett. 2007; 9: 2421

18a Kulinkovich OG. Chem. Rev. 2003; 103: 2597
18b Rubin M. Rubina M. Gevorgyan V. Chem. Rev. 2007; 107: 3117
18c Yu M. Pagenkopf BL. Tetrahedron 2005; 61: 321
18d Du D. Wang Z. Tetrahedron Lett. 2008; 49: 956

19 Xie YX. Yan ZY. Wang DZ. Wu LY. Qian B. Liu XY. Liang YM. Eur. J. Org. Chem. 2009; 40: 2283
20 Honda M. Mita T. Nishizawa T. Sano T. Segi M. Nakajima T. Tetrahedron Lett. 2006; 47: 5751
21 Fischer H. Tomeba NK. Pahadi NT. Patil Z. Yamamoto Y. J. Am. Chem. Soc. 2008; 130: 15720

Zusatzmaterial

Supporting Information