Recent Advances in the Chemistry of 2-Acylaziridines

Alena S. Pankova; Mikhail A. Kuznetsov

doi:10.1055/s-0036-1590889

Synthesis, Table of Contents

Synthesis 2017; 49(23): 5093-5104
DOI: 10.1055/s-0036-1590889

short review

Recent Advances in the Chemistry of 2-Acylaziridines

Alena S. Pankova*

Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation Email: a.pankova@spbu.ru Email: m.kuznetsov@spbu.ru

,

Mikhail A. Kuznetsov*

Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation Email: a.pankova@spbu.ru Email: m.kuznetsov@spbu.ru

› Author Affiliations

Abstract

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Abstract

This review highlights recent achievements in the transformations of 2-acylaziridines toward the synthesis of cyclic and acyclic nitrogen-containing compounds. The influence of a carbonyl group on reaction selectivity is discussed.

1 Introduction

2 Reactions via C–C Bond Cleavage

3 Reactions via C–N Bond Cleavage

3.1 Reactions Starting with the Aziridine Ring Opening

3.2 Reactions Starting at the Carbonyl Group

4 Conclusion

Key words

aziridines - carbonyl group - nitrogen heterocycles - synthetic methods - cascade reactions

Full Text

References

References

1a Aziridines and Epoxides in Organic Synthesis. Yudin AK. Wiley-VCH; Weinheim: 2006
1b Padwa A. In Comprehensive Heterocyclic Chemistry III . Vol. 1. Katritzky AR. Ramsden CA. Scriven EF. V. Taylor RJ. K. Elsevier; Oxford: 2008: 1
1c Sweeney JB. Chem. Soc. Rev. 2002; 31: 247
1d Degennaro L. Trinchera P. Luisi R. Chem. Rev. 2014; 114: 7881
1e Florio S. Luisi R. Chem. Rev. 2010; 110: 5128
1f Pellissier H. Adv. Synth. Catal. 2014; 356: 1899
1g Ismail FM. D. Levitsky DO. Dembitsky VM. Eur. J. Med. Chem. 2009; 44: 3373
1h Singh GS. Mini-Rev. Med. Chem. 2016; 16: 892
1i Feng J.-J. Zhang J. ACS Catal. 2016; 6: 6651

For reviews on other types of aziridines, see:

2a N–H ketoaziridines: Samimi HA. Mini-Rev. Org. Chem. 2015; 12: 328
2b Aziridine-2-carboxylates: Ishikawa T. Heterocycles 2012; 85: 2837
2c Vinylaziridines: Heo YM. Paek S.-M. Molecules 2013; 18: 9650
2d Vinyl- and ethynylaziridines: Ohno H. Chem. Rev. 2014; 114: 7784
2e Methyleneaziridines: Shipman M. Synlett 2006; 3205
2f Methyleneaziridines: Tehrani KA. De Kimpe N. Curr. Org. Chem. 2009; 13: 854
2g Carbohydrate aziridines: Karban J. Kroutil J. Adv. Carbohydr. Chem. Biochem. 2006; 60: 27
2h C-Heteroatom-substituted aziridines: Singh GS. D’hooghe M. De Kimpe N. Chem. Rev. 2007; 107: 2080
2i Aziridine-1-carbaldehyde oximes: Nikitjuka A. Jirgensons A. Chem. Heterocycl. Compd. 2014; 49: 1544
2j 2-(Carboxymethyl)aziridine derivatives: Callebaut G. Meiresonne T. De Kimpe N. Mangelinckx S. Chem. Rev. 2014; 114: 7954

3a Lown JW. In 1,3-Dipolar Cycloaddition Chemistry . Vol. 1. Padwa A. John Wiley; New York: 1984: 653
3b Harwood LM. Vickers RJ. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products. Vol. 59. Padwa A. Pearson WH. Wiley; Hoboken: 2003: 169
3c Coldham I. Hufton R. Chem. Rev. 2005; 105: 2765
3d Huisgen R. Sheer W. Huber H. J. Am. Chem. Soc. 1967; 89: 1753

4 Kuznetsov MA. Kuznetsova LM. Pankova AS. Tetrahedron Lett. 2016; 57: 3575
5 Beletskii EV. Kuznetsov MA. Russ. J. Org. Chem. 2009; 45: 1229
6 Pankova AS. Stukalov AYu. Kuznetsov MA. Org. Lett. 2015; 17: 1826
7 Kuznetsov MA. Voronin VV. Chem. Heterocycl. Compd. 2011; 47: 173
8 Kuznetsov MA. Voronin VV. Russ. J. Org. Chem. 2013; 49: 83
9 Pankova AS. Kuznetsov MA. Tetrahedron Lett. 2014; 55: 2499
10 Samimi HA. Mohammadi S. Synlett 2013; 24: 223
11 Samimi HA. Entezami S. J. Chem. Res. 2013; 37: 745
12 Samimi HA. Dadvar F. Synthesis 2015; 47: 1899

13a Ribeiro Laia FM. Cardoso AL. Beja AM. Silva MR. Pinho e Melo TM. V. D. Tetrahedron 2010; 66: 8815
13b Cardoso AL. Henriques MS. C. Paixão JA. Pinho e Melo TM. V. D. J. Org. Chem. 2016; 81: 9028

14 Cardoso AL. Nunes RM. D. Arnaut LG. Pinho e Melo TM. V. D. Synthesis 2011; 3516
15 Ribeiro Laia FM. Pinho e Melo TM. V. D. Synthesis 2015; 47: 2781
16 Miyamoto Y. Wada N. Soeta T. Fujinami S. Inomata K. Ukaji Y. Chem. Asian J. 2013; 8: 824
17 Malatesti N. Boa AN. Clark S. Westwood R. Tetrahedron Lett. 2006; 47: 5139
18 Wang S. Zhu X. Chai Z. Wang S. Org. Biomol. Chem. 2014; 12: 1351
19 Wei L. Zhang J. Chem. Commun. 2012; 48: 2636

20a Stankovic S. D’hooghe M. Catak S. Eum H. Waroquier M. Van Speybroeck V. De Kimpe N. Ha H.-J. Chem. Soc. Rev. 2012; 41: 643
20b Hu XE. Tetrahedron 2004; 60: 2701
20c Cardoso AL. Pinho e Melo TM. V. D. Eur. J. Org. Chem. 2012; 6479

21 Yook C.-M. Eum H. Ha H.-J. Kang KY. Lee WK. Bull. Korean Chem. Soc. 2011; 32: 2879
22 Kim Y. Ha H.-J. Yun H. Lee BK. Lee WK. Tetrahedron 2006; 62: 8844
23 Tang C.-Y. Wang G. Yang X.-Y. Wu X.-Y. Sha F. Tetrahedron Lett. 2014; 55: 6447
24 Samimi HA. Mohammadi S. J. Iran. Chem. Soc. 2014; 11: 69
25 Barros MT. Dey SS. Maycock CD. Rodrigues P. Tetrahedron 2012; 68: 6263
26 Cruz DC. Sanchez-Murcia PA. Jørgensen KA. Chem. Commun. 2012; 48: 6112
27 Samimi HA. Mamaghani M. Tabatabaeian K. J. Heterocycl. Chem. 2008; 45: 1765
28 Samimi HA. Shams Z. J. Heterocycl. Chem. 2014; 51: 1659
29 Samimi HA. Mostafavi A. Farsani MR. J. Iran. Chem. Soc. 2015; 12: 2031
30 Samimi HA. Yamin BM. Soltani M. J. Iran. Chem. Soc. 2014; 11: 1467
31 Samimi HA. Yamin BM. J. Chem. Res. 2014; 38: 358
32 Han Y. Xie Y.-X. Zhao L.-B. Fan M.-J. Liang Y.-M. Synthesis 2008; 87
33 Cui S.-L. Wang J. Wang Y.-G. Org. Lett. 2007; 9: 5023
34 Zhu Y. Wang S. Wen S. Lu P. Wang Y. Tetrahedron Lett. 2010; 51: 4763
35 Mahmoodi NO. Yazdanbakhsh MR. Kiyani H. Sharifzadeh B. J. Chin. Chem. Soc. 2007; 54: 635

36a Mahmoodi NO. Ghavidast A. Mirkhaef S. Zanjanchi MA. Dyes Pigm. 2015; 118: 110
36b Mahmoodi NO. Mirkhaef S. Ghavidast A. J. Mol. Struct. 2015; 1081: 248
36c Kiyani H. Fallahnezhad S. Albooyeh F. Lett. Org. Chem. 2015; 12: 168 ; and references cited therein

37 Samimi HA. Yamin BM. Tetrahedron Lett. 2016; 57: 223
38 Samimi HA. Yamin BM. Saberi F. Synthesis 2015; 47: 129
39 Du X. Yang S. Yang J. Liu Y. Chem. Eur. J. 2011; 17: 4981
40 Samimi HA. Shams Z. Momeni AR. J. Iran. Chem. Soc. 2012; 9: 705
41 Samimi HA. Kiyani H. Shams Z. J. Chem. Res. 2013; 37: 282
42 Samimi HA. Salehi E. Dadvar F. J. Chem. Res. 2014; 38: 731
43 Larraufie M.-H. Pellet R. Fensterbank L. Goddard J.-P. Lacote E. Malacria M. Ollivier C. Angew. Chem. Int. Ed. 2011; 50: 4463
44 Davis AL. Korous AA. Hartel AM. Tetrahedron Lett. 2013; 54: 3673
45 Cui S.-L. Wang J. Wang Y.-G. Org. Lett. 2008; 10: 13
46 Silva S. Rodrigues P. Bento I. Maycock CD. J. Org. Chem. 2015; 80: 3067
47 Jiang H. Holub N. Jørgensen KA. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 20630
48 Chen G. Sasaki M. Yudin AK. Tetrahedron Lett. 2006; 47: 255