Evolution of the Aza-Diels–Alder Reaction of 2H-Azirines

Hao Zhou; Mei-Hua Shen; Hua-Dong Xu

doi:10.1055/s-0035-1562493

Synlett, Table of Contents

Synlett 2016; 27(15): 2171-2177
DOI: 10.1055/s-0035-1562493

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Evolution of the Aza-Diels–Alder Reaction of 2H-Azirines

Authors

Hao Zhou

School of Pharmaceutical Engineering and Life Science, Changzhou University, 1 Middle Gehu Rd., Changzhou, Jiangsu Province, 213164, P. R. of China Email: shenmh@cczu.edu.cn Email: huadongxu@gmail.com
Mei-Hua Shen*

School of Pharmaceutical Engineering and Life Science, Changzhou University, 1 Middle Gehu Rd., Changzhou, Jiangsu Province, 213164, P. R. of China Email: shenmh@cczu.edu.cn Email: huadongxu@gmail.com
Hua-Dong Xu*

School of Pharmaceutical Engineering and Life Science, Changzhou University, 1 Middle Gehu Rd., Changzhou, Jiangsu Province, 213164, P. R. of China Email: shenmh@cczu.edu.cn Email: huadongxu@gmail.com

Abstract

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Abstract

The aza-Diels–Alder reaction of 2H-azirines with 1,3-dienes provides facile access to the structurally intriguing and difficult to access 1-azabicyclo[4.1.0]hept-3-ene scaffold. Its application in organic synthesis and medicinal chemistry is heavily hampered by the narrow substrate scope for both reacting partners. Herein, the discovery and exploration of this reaction are summarized and discussed. A recent breakthrough is an intramolecular version that overcomes the limitations of conventional methods.

Key words

aza-Diels–Alder reaction - 2H-azirines - vinyl azide - intramolecular Diels–Alder reaction - N-heterocycles

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References

References

1a Hassner A, Anderson DJ. J. Am. Chem. Soc. 1971; 93: 4339
1b Hassner A, Anderson DJ. J. Am. Chem. Soc. 1972; 94: 8255
1c Anderson DJ, Hassner A. J. Org. Chem. 1973; 38: 2565
1d Nair V. J. Org. Chem. 1972; 37: 802

2a Hassner A, Anderson DJ. J. Org. Chem. 1974; 39: 2031
2b Nair V. J. Org. Chem. 1972; 37: 2508

3a Bhullar P, Gilchrist TL, Maddocks P. Synthesis 1997; 271
3b Alves MJ, Gilchrist TL. Tetrahedron Lett. 1998; 39: 7579
3c Alves MJ, Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1998; 299
3d Gilchrist TL, Mendonca R. ARKIVOC 2000; (i): 769

4 Alves MJ, Bickley JF, Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1999; 1399

5a Ray CA, Risberg E, Somfai P. Tetrahedron Lett. 2001; 42: 9289
5b Ray CA, Risberg E, Somfai P. Tetrahedron 2002; 58: 5983
5c Sjöholm-Timén Å, Somfai P. J. Org. Chem. 2003; 68: 9958
5d Timen AS, Fischer A, Somfai P. Chem. Commun. 2003; 1150

6 Timen S, Somfai P. J. Org. Chem. 2003; 68: 9958

7a Davis FA, Wu Y, Yan H, Prasad KR, McCoull W. Org. Lett. 2002; 4: 655
7b Davis FA, Deng J. Org. Lett. 2007; 9: 1707

8a Alves MJ, Fortes AG, Costa FT. Tetrahedron 2006; 62: 3095
8b Alves MJ, Fortes AG, Costa FT, Duarte VC. M. Tetrahedron 2007; 63: 11167

9a Alves MJ, Costa C, Duraes MM. Tetrahedron: Asymmetry 2009; 20: 1378
9b Alves MJ, Durães MM, Fortes AG. Tetrahedron Lett. 2003; 44: 5079
9c Alves MJ, Durães MM, Fortes AG. Tetrahedron 2004; 60: 6541

10a Banert K, Meier B. Angew. Chem. Int. Ed. 2006; 45: 4015
10b Banert K, Ihle A, Kuhtz A, Penk E, Saha B, Würthwein E.-U. Tetrahedron 2013; 69: 2501

11 Xu H.-D, Zhou H, Pan Y.-P, Ren X.-T, Wu H, Han M, Han R.-Z, Shen M.-H. Angew. Chem. Int. Ed. 2016; 55: 2540
12 Gilchrist TL. Aldrichimica Acta 2001; 34: 51

13a Zi W, Zuo Z, Ma D. Acc. Chem. Res. 2015; 48: 702
13b Mercado-Marin EV, Garcia-Reynaga P, Romminger S, Pimenta EF, Romney DK, Lodewyk MW, Williams DE, Andersen RJ, Miller SJ, Tantillo DJ, Berlinck RG. S, Sarpong R. Nature 2014; 509: 318
13c Crossley SW. M, Shenvi RA. Chem. Rev. 2015; 115: 9465

14 Xu H.-D, Jia Z.-H, Xu K, Han M, Jiang S.-N, Cao J, Wang J.-C, Shen M.-H. Angew. Chem. Int. Ed. 2014; 53: 9284