Multicomponent Reactions in the Synthesis of γ-Lactams

Edorta Martinez de Marigorta; Jesús M. de los Santos; Ana M. Ochoa de Retana; Javier Vicario; Francisco Palacios

doi:10.1055/s-0037-1611014

Synthesis, Table of Contents

Synthesis 2018; 50(23): 4539-4554
DOI: 10.1055/s-0037-1611014

short review

Multicomponent Reactions in the Synthesis of γ-Lactams

Edorta Martinez de Marigorta

,

Jesús M. de los Santos

,

Ana M. Ochoa de Retana

,

Javier Vicario *

,

Francisco Palacios *

Abstract

All articles of this category

Abstract

This review summarizes the synthesis of γ-lactam ring using multicomponent reactions.

1 Introduction

2 Pyrrolidin-2-ones

3 Pyrrolin-2-ones (Dihydro-2H-pyrrol-2-ones)

4 Final Remarks

Key words

multicomponent reactions - γ-lactams - pyrrolidin-2-ones - pyrrolin-2-ones - dihydro-2H-pyrrol-2-ones

Full Text

References

References
1 Caruano J. Muccioli GG. Robiette R. Org. Biomol. Chem. 2016; 14: 10134
2 Abou-Khali B. Neuropsychiatr. Dis. Treat. 2006; 4: 507
3 Schwartz RE. Helms GL. Bolessa EA. Wilson KE. Giacobbe RA. Tkacz JS. Bills GF. Liesch JM. Zink DL. Curotto JE. Pramanik B. Onishi JC. Tetrahedron 1994; 50: 1675
4 Osterhage C. Kaminski R. König GM. Wright AD. J. Org. Chem. 2000; 65: 6412
5 Janecka A. Wyrȩbska A. Gach K. Fichna J. Janecki T. Drug Discovery Today 2012; 17: 561
6 Bioactive Marine Natural Products . Bhakuni DS. Rawat DS. Springer; Dordrecht: 2005

For reviews see:

7a Martelli G. Orena M. Rinaldi S. Curr. Org. Chem. 2014; 18: 1373
7b Martelli G. Monsignori A. Orena M. Rinaldi S. Curr. Org. Chem. 2014; 18: 1539
7c Pelkey ET. Pelkey SJ. Greger JG. Adv. Heterocycl. Chem. 2015; 115: 151

8 Schreiber SL. Science 2000; 287: 1964

9a Ramón DJ. Yus M. Angew. Chem. Int. Ed. 2005; 44: 1602
9b Multicomponent Reactions in Organic Synthesis . Zhu J. Wang Q. Wang M.-X. Wiley-VCH; Weinheim: 2015

10 Chatani N. Tobisu M. Asaumi T. Murai S. Synthesis 2000; 925
11 Huo C. Yuan Y. J. Org. Chem. 2015; 80: 12704
12 Bianchi L. Ballerini E. Curini M. Lanari D. Marrocchi A. Oldani C. Vaccaro L. ACS Sustainable Chem. Eng. 2015; 3: 1873
13 Paul J. Presset M. Le Gall E. Léonel E. Retailleau P. Synthesis 2018; 50: 254
14 Xu Y. Huang D. Wang K.-H. Ma J. Su Y. Fu Y. Hu Y. J. Org. Chem. 2015; 80: 12224
15 Jiang H. Tian Y. Tian L. Li J. RSC Adv. 2017; 7: 32300
16 Xu S. Su S. Zhang H. Tian L. Liang P. Chen J. Zhang Y. Li C. Jia X. Li J. Synthesis 2015; 47: 2414
17 Cioc RC. van Riempst LS. Schuckman P. Ruijter E. Orru RV. Synthesis 2017; 49: 1664
18 Che C. Li S. Jiang X. Quan J. Lin S. Yang Z. Org. Lett. 2010; 12: 4682
19 Ghandi M. Khodadadi M. Abbasi A. J. Iran Chem. Soc. 2016; 13: 1691
20 Gao Q. Hao W.-J. Liu F. Tu S.-J. Wang S.-L. Li G. Jiang B. Chem. Commun. 2016; 52: 900
21 He Y.-T. Li L.-H. Zhou Z.-Z. Hua H.-L. Qiu Y.-F. Liu X.-Y. Liang Y.-M. Org. Lett. 2014; 16: 3896
22 Esmaeili AA. Khoddam-Mohhammadi H. Moradi A. Davamdar E. Izaydar M. Khavani M. Islamin MR. RSC Adv. 2014; 4: 37900
23 de Gracia Retamosa M. Ruiz-Olalla A. Bello T. de Cózar A. Cossío FP. Angew. Chem. Int. Ed. 2018; 57: 668
24 Hoshimoto Y. Ohata T. Sasaoka Y. Ohashi M. Ogoshi S. J. Am. Chem. Soc. 2014; 136: 15877
25 Ogoshi S. Ikeda H. Kurosawa H. Angew. Chem. Int. Ed. 2007; 46: 4930
26 Fukuyama T. Nakashima N. Okada T. Ryu I. J. Am. Chem. Soc. 2013; 135: 1006
27 Ozawa T. Horie H. Kurahashi T. Matsubara S. Chem. Commun. 2010; 46: 8055
28 Metten B. Kostermans M. Van Baelen G. Smet M. Dehaen W. Tetrahedron 2006; 62: 6018
29 Mohammat MF. Shaameri Z. Hamzah AS. Molecules 2009; 14: 250
30 Gein VL. Tsyplyakova EP. Stashina GA. Bakulev VA. Russ. J. Org. Chem. 2008; 44: 478
31 Gein VL. Mar’yasov MA. Russ. J. Org. Chem. 2015; 51: 110
32 Vydzhak RN. Panchishin SY. Russ. J. Gen. Chem. 2008; 78: 1641
33 Kawasuji T. Fuji M. Yoshinaga T. Sato A. Fujiwara T. Kiyama R. Bioorg. Med. Chem. 2007; 15: 5487
34 Gein VL. Kasimova NN. Aliev ZG. Vakhrin MI. Russ. J. Org. Chem. 2010; 46: 875
35 Shymanska NV. Pierce JG. Org. Lett. 2017; 19: 2961
36 Gein VL. Yushkov VV. Splina TA. Gein LF. Yatsenko KV. Shevtsova SG. Pharm. Chem. J. 2008; 42: 255
37 Gao Y. Samanta S. Cui T. Lam Y. ChemMedChem 2013; 8: 1554
38 Palacios F. Vicario J. Aparicio D. Eur. J. Org. Chem. 2006; 2843
39 Li X. Deng H. Luo S. Cheng J.-P. Eur. J. Org. Chem. 2008; 4350
40 Ghashang M. Res. Chem. Intermed. 2013; 39: 2187
41 Reza M. Shafiee M. Najafabadi BH. Ghashang M. J. Chem. Res. 2011; 35: 634
42 Ghashang M. Shaterian HR. Chin. J. Chem. 2011; 29: 1851
43 Shaterian HR. Ranjbar M. Res. Chem. Intermed. 2014; 40: 2059
44 Niknam K. Mojikhalifeh S. Mol. Diversity 2014; 18: 111
45 del Corte X. Maestro A. Vicario J. Martinez de Marigorta E. Palacios F. Org. Lett. 2018; 20: 317
46 Gao H. Sun J. Yan C.-G. Tetrahedron 2013; 69: 589
47 Khan AT. Gosh A. Khan MM. Tetrahedron Lett. 2012; 53: 2622
48 Saha M. Das AR. ChemistrySelect 2017; 2: 10249
49 Zhu Q. Jiang H. Li J. Liu S. Xia C. Zhang M. J. Comb. Chem. 2009; 11: 685

50a Nair V. Mathen JS. Vinod AU. Varma RL. Chem. Lett. 2001; 738
50b Nair V. Mathen JS. Viji S. Srinivas R. Nandakumar MV. Varma RL. Tetrahedron 2002; 58: 8113

51 Fan M.-F. Quian B. Zhao L.-B. Liang Y.-M. Tetrahedron 2007; 63: 8987
52 Quai M. Frattini S. Vendrame U. Mondoni M. Dossena S. Cereda E. Tetrahedron Lett. 2004; 45: 1413
53 Tang Z. Liu Z. An Y. Jiang R. Zhang X. Li C. Jia X. Li J. J. Org. Chem. 2016; 81: 9158
54 Kumari S. Rajeswari M. Khurana JM. Synth. Commun. 2016; 46: 387
55 Oon IC. Cho CS. Appl. Organometal. Chem. 2015; 29: 226
56 Gao Q. Liu S. Wu X. Wu A. Tetrahedron Lett. 2014; 55: 6403
57 Lin Y.-W. Deng J.-C. Hsieh Y.-Z. Chuang S.-C. Org. Biomol. Chem. 2014; 12: 162
58 Deng J.-C. Chen W.-Y. Zhu C. Chuang S.-C. Adv. Synth. Catal. 2015; 357: 1453