Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2021; 53(12): 2081-2091
DOI: 10.1055/s-0040-1706660
DOI: 10.1055/s-0040-1706660
paper
A Cascade Process of Hydroxamates Renders 1,6-Dioxa-3,9-diazaspiro[4.4]nonane-2,8-diones
The authors are grateful for financial support from Monash University through the award of a Ph.D. scholarship to Z.N.
![](https://www.thieme-connect.de/media/synthesis/202112/lookinside/thumbnails/ss-2020-f0559-op_10-1055_s-0040-1706660-1.jpg)
Abstract
A cascade route to 1,6-dioxa-3,9-diazaspiro[4.4]nonane-2,8-diones from N,O-diacyl hydroxylamines consisting of a two-step procedure is described. The key transformation is a [3,3]-sigmatropic rearrangement of N,O-diacyl hydroxylamines promoted by formation of a silylketenaminal followed by an intramolecular cyclization and a final spirocyclization. The optimum reaction conditions employ a one-fold excess of each reagent and are utilized to prepare a range of structurally diverse examples of this class of compound.
Key words
[3,3]-sigmatropic rearrangement - cascade process - N,O-diacyl hydroxylamines - 3-azaspirocyclic orthoamides - 1,6-dioxa-3,9-diazaspiro[4.4]nonane-2,8-dionesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706660.
- Supporting Information
Publication History
Received: 29 October 2020
Accepted after revision: 08 December 2020
Article published online:
19 January 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Ziegler FE. Chem. Rev. 1988; 88: 1423
- 2 Overman LE. Angew. Chem., Int. Ed. Engl. 1984; 23: 579
- 3 Blechert S. Synthesis 1989; 71
- 4 Magedov IV, Smushkevich YI. J. Chem. Soc., Chem. Commun. 1990; 1686
- 5 Endo Y, Shudo K. Tetrahedron Lett. 1991; 32: 4517
- 6 Endo Y, Uchida T, Hizatate S, Shudo K. Synthesis 1994; 1096
- 7 Miller SJ, Bayne CD. J. Org. Chem. 1997; 62: 5680
- 8 Al-Faiyz YS. S, Clark AJ, Filik RP, Peacock JL, Thomas GH. Tetrahedron Lett. 1998; 39: 1269
- 9 Clark AJ, Al-Faiyz YS. S, Broadhurst MJ, Patel D, Peacock JL. J. Chem. Soc., Perkin Trans. 1 2000; 1117
- 10 Clark AJ, Al-Faiyz YS. S, Patel D, Broadhurst MJ. Tetrahedron Lett. 2001; 42: 2007
- 11 Lagiakos HR, Aguilar M.-I, Perlmutter P. J. Org. Chem. 2009; 74: 8001
- 12 Ito Y, Konoike T, Saegusa T. J. Am. Chem. Soc. 1975; 97: 2912
- 13 Paquette LA, Bzowej EI, Branan BM, Stanton KJ. J. Org. Chem. 1995; 60: 7277
- 14 Matsumura Y, Nishimura M, Hiu H, Watanabe M, Kise N. J. Org. Chem. 1996; 61: 2809
- 15 Nazarian Z, Forsyth C. RSC Adv. 2016; 6: 55534
- 16 Price BJ, Sutherland IO. Chem. Commun. (London) 1967; 1070
-
17 Parallel research in our laboratory revealed that N,O-diacyl hydroxyl amine derivatives can undergo 3,3-sigmatropic rearrangement under different conditions.
- 18 Forsyth CM, Nazarian Z. IUCrData 2019; 4: x190520
- 19 Hoffman RV, Nayyar NK, Chen W. J. Org. Chem. 1992; 57: 5700
- 20 Keck GE, Wager TT, McHardy SF. Tetrahedron 1999; 55: 11755