Direct Synthesis of Vicinal Tricarbonyl Amides by Coupling of α-Oxo Acid Chlorides with Carbamoylsilanes

Yuling Han; Yuping Li; Shenghua Han; Pengpeng Zhang; Jianxin Chen

doi:10.1055/s-0037-1611778

Synthesis, Table of Contents

Synthesis 2019; 51(15): 2977-2983
DOI: 10.1055/s-0037-1611778

paper

Direct Synthesis of Vicinal Tricarbonyl Amides by Coupling of α-Oxo Acid Chlorides with Carbamoylsilanes

Yuling Han

^aCollege of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004, P. R. China

,

Yuping Li

^aCollege of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004, P. R. China

,

Shenghua Han

^bCollege of Chemistry and Engineering, Shanxi Datong University, Datong 037009, P. R. China Email: jjxxcc2002@126.com Email: chenjx@sxnu.edu.cn

,

Pengpeng Zhang

^aCollege of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004, P. R. China

,

Jianxin Chen*

^aCollege of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004, P. R. China

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Abstract

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Abstract

A convenient synthetic method for vicinal tricarbonyl amides by the cross-coupling reaction of α-oxo acid chlorides with carbamoylsilanes is developed. The reaction tolerates a broad range of substituents on the amido nitrogen of carbamoylsilanes, and directly affords good yields of vicinal tricarbonyl amides under mild conditions without use of oxidants. The reaction of carbamoylsilanes with oxalyl chloride has also been explored, and is accompanied by decarbonylation to give vicinal tricarbonyl amides.

Key words

α-oxo acid chlorides - carbamoylsilanes - vicinal tricarbonyl compounds - aminocarbonylation - synthetic methods

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References

References

1a Adlington RM, Baldwin JE, Catterickand D, Pritchard GJ. J. Chem. Soc., Perkin Trans. 1 2001; 668
1b Altuna-Urquijo M, Gehre A, Stanforth SP, Tarbit B. Tetrahedron 2009; 65: 975
1c Wasserman HH, Rotello VM, Krause GB. Tetrahedron Lett. 1992; 33: 5419
1d Wasserman HH, Chenand JH, Xia M. J. Am. Chem. Soc. 1999; 121: 1401
1e Robach J, Baumeister J, Harms K, Koert U. Eur. J. Org. Chem. 2013; 662
1f Loosley BC, Andersen RJ, Dake GR. Org. Lett. 2013; 15: 1152
1g Robbach J, Harms K, Koert U. Eur. J. Org. Chem. 2014; 993
1h Robbach J, Harms K, Koert U. Org. Lett. 2015; 17: 3122
1i Yuki T, Yonekawa M, Matsumoto K, Sei Y, Tomita I, Endo T. Tetrahedron 2016; 65: 4783
1j Yuki T, Yonekawa M, Furusho Y, Sei Y, Tomita I, Endo T. Tetrahedron 2016; 65: 2868

2a Wasserman HH, Rotello VM. J. Org. Chem. 1989; 54: 2785
2b Jones TK, Mills SG, Reamer RA, Askin D, Desmond R, Volante RP, Shinkai I. J. Am. Chem. Soc. 1989; 111: 1157
2c Tanaka H, Kuroda A, Marusawa H, Hatanaka H, Kino T, Goto T, Hashimoto M, Taga T. J. Am. Chem. Soc. 1987; 109: 5031
2d Matsushita K, Suzuki K, Ohmori K. Synlett 2017; 28: 944

3a Rubin MB, Gleiter R. Chem. Rev. 2000; 100: 1121
3b Wasserman HH, Parr J. Acc. Chem. Res. 2004; 37: 687
3c Batchelor MJ, Gillespie RJ, Golec JM. C, Hedgecoch CJ. R. Tetrahedron Lett. 1993; 34: 167
3d Wasserman HH, Pichett JE. J. Am. Chem. Soc. 1982; 104: 4695
3e Asahara H, Nishiwaki N. J. Org. Chem. 2014; 79: 11735
3f Lai JH, Pham H, Hangauer DG. J. Org. Chem. 1996; 61: 1872
3g Santos MS, Coelho F. RSC Adv. 2012; 2: 3237
3h Wasserman HH, Ennis DS, Power PL, Ross MJ, Gomes B. J. Org. Chem. 1993; 58: 4785
3i Robbach J, Baumeister J, Harms K, Koert U. Eur. J. Org. Chem. 2013; 662
3j Hoffman RV, Kim HO, Wilson AL. J. Org. Chem. 1990; 55: 2820
3k Mahran MR, Abdou WM, Sidky MM, Wamhoff H. Synthesis 1987; 506
3l Lee K, Im JM. Tetrahedron Lett. 2001; 42: 1539

4a Baranac-Stojanovic M, Markovic R, Stojanovic M. Tetrahedron 2011; 67: 8000
4b Wang L.-Z, Li H.-L, Ge L.-S, An X.-L, Zhang Z.-G, Luo X, Fossey JS, Deng W.-P. J. Org. Chem. 2014; 79: 1156
4c Wang L.-Z, An X.-L, Ge L.-S, Jin J.-H, Luo X.-Y, Deng W.-P. Tetrahedron 2014; 70: 3788
4d Sivan A, Deepth A. Tetrahedron Lett. 2014; 55: 1890
4e Cui J, Duan Y.-N, Yu J, Zhang C. Org. Chem. Front. 2016; 3: 1686
4f Liu Y.-Y, Zhang Z.-G, Wan Y.-M, Zhang G.-S, Li Z.-L, Bi J.-G, Ma N.-N, Liu T.-X, Liu Q.-F. J. Org. Chem. 2017; 82: 3901

5a Tong W.-T, Liu H, Chen J.-X. Tetrahedron Lett. 2015; 56: 1335
5b Liu H, Guo Q.-L, Chen J.-X. Tetrahedron Lett. 2015; 56: 5747
5c Guo Q.-L, Wen X.-P, Chen J.-X. Tetrahedron 2016; 72: 8117

6a Cao P, Wen X.-P, Chen J.-X. Synlett 2017; 28: 353
6b Li W.-D, Han Y.-L, Chen J.-X. Tetrahedron 2017; 73: 5813
6c Yao Y, Li W.-D, Tong W.-T, Chen J.-X. Chin. J. Org. Chem. 2015; 35: 223
6d Li W.-D, Liu Y.-H, Chen J.-X. Tetrahedron Lett. 2015; 56: 4328
6e Yao Y, Li W.-D, Chen J.-X. Chin. J. Org. Chem. 2014; 34: 2124
6f Chen X.-J, Chen J.-X. Mendeleev Commun. 2013; 23: 106

7a Zhang W.-J, Han S.-H, Chen J.-X. Synth. Commun. 2017; 47: 704
7b Tong W.-T, Cao P, Liu Y.-H, Chen J.-X. J. Org. Chem. 2017; 82: 11603
7c Wen X.-P, Han Y.-L, Chen J.-X. RSC Adv. 2017; 7: 45107
7d Zhang W.-J, Cao P, Guo Q.-L, Chen J.-X. Curr. Org. Synth. 2017; 14: 1067

8 For the preparation of the carbamoylsilanes, see: Cunico RF, Chen J.-X. Synth. Commun. 2003; 33: 1963
9 Yonekawa M, Furusho Y, Sei Y, Takata T, Endo T. Tetrahedron 2013; 69: 4076
10 Schöllkopf U, Beckhaus H. Angew. Chem., Int. Ed. Engl. 1976; 15: 293
11 Davies SG, Ichihara O. Tetrahedron Lett. 1998; 39: 6045
12 Yuki T, Yonekawa M, Furusho Y, Sei Y, Tomita I, Endo T. Tetrahedron 2016; 72: 2868

13a Cunico RF, Motta AR. Org. Lett. 2005; 7: 771
13b Cunico RF, Pandey RK. J. Org. Chem. 2005; 70: 9048

14 Malmberg WD, Vob J, Weinschneider S. Liebigs Ann. Chem. 1983; 1694

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