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 2018; 50(10): 2094-2098
DOI: 10.1055/s-0037-1609363
DOI: 10.1055/s-0037-1609363
paper
A Novel Diazomethane-Mediated Synthesis of Azetidine-Embedded Tetracyclic Ketal Systems
This work was partially supported by the Department of Science and Technology (DST), New DelhiFurther Information
Publication History
Received: 08 December 2017
Accepted after revision: 22 February 2018
Publication Date:
22 March 2018 (online)
Abstract
Herein, the first diazomethane-mediated synthesis of azetidine-embedded tetracyclic ketal systems is reported. Reactions of norbornyl hemiaminal acetals with diazomethane afford azetidine-embedded tetracyclic ketals in good to excellent yields. The bridgehead-bromo-substituted hemiaminal acetals give higher yields compared to the corresponding bridgehead-chloro-substituted hemiaminal acetals. The hemiaminal acetals are prepared stereoselectively via nucleophilic addition of various amines to norbornyl α-diketones from the exo face.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609363.
- Supporting Information
-
References
- 1 Present address: G. H. M. Rao, Department of Chemistry, Texila American University, Georgetown, Guyana, South America.
- 2a Honcharenko D. Varghese OP. Plashkevych O. Barman J. Chattopadhyaya J. J. Org. Chem. 2006; 71: 299
- 2b Evans GB. Furneaux RH. Greatrex B. Murkin AS. Schramm VL. Tyler PC. J. Med. Chem. 2008; 51: 948
- 2c Ji J. Bunnelle WH. Li T. Pace JM. Schrimpf MR. Sippy KB. Anderson DJ. Meyer MD. Pure Appl. Chem. 2005; 77: 2041
- 3a Oike H. Washizuka M. Tezuka Y. Macromol. Chem. Phys. 2000; 201: 1673
- 3b Kuo M.-C. Jeng R.-J. Su W.-C. Dai S. Macromolecules 2008; 41: 682
- 3c Wang S.-C. Chen P.-C. Yeh J.-T. Chen K.-N. React. Funct. Polym. 2007; 67: 299
- 4a Almens J. Foubelo F. Yus M. Tetrahedron 1994; 50: 5775
- 4b Banide E. de Talancé VL. Schmidt G. Lubin H. Comesse S. Dechoux L. Hamon L. Kadouri-Puchot C. Eur. J. Org. Chem. 2007; 4517
- 5a Zi GF. Liu RC. Bai XM. Zhang ZB. Appl. Organomet. Chem. 2008; 22: 671
- 5b Couty F. Prim D. Tetrahedron: Asymmetry 2002; 13: 2619
- 6a De Kimpe N. In Comprehensive Heterocyclic Chemistry II . Vol. 1B. Padwa A. Chap 1.18 Elsevier; Oxford: 1996: p 507
- 6b Moore JA. Ayers RS. In Chemistry of Heterocyclic Compounds, Small Ring Heterocycles . Hassner A. Wiley; New York: 1983. Part 3 p 1
- 6c Cromwell NH. Phillips B. Chem. Rev. 1979; 79: 331
- 7a Kobayashi J. Ishibashi M. Heterocycles 1996; 42: 943
- 7b Shuman RT. Rothenberger RB. Campbell CS. Smith GF. Gifford-Moore DS. J. Med. Chem. 1995; 38: 4446
- 8a Ungureanu I. Klotz P. Schoenfelder A. Mann A. Chem. Commun. 2001; 958
- 8b Ungureanu I. Klotz P. Schoenfelder A. Mann A. Tetrahedron Lett. 2001; 42: 6087
- 8c Prasad BA. B. Bisai A. Singh VK. Org. Lett. 2004; 6: 4829
- 9a Van Brabandt W. Mangelinckx S. D’hooghe M. Van Driessche B. De Kimpe N. Curr. Org. Chem. 2009; 13: 827
- 9b Couty F. Evano G. Prim D. Mini-Rev. Org. Chem. 2004; 1: 133
- 10a Vaughan WR. Klonowski RS. McEilhinney RS. Millward BB. J. Org. Chem. 1961; 26: 138
- 10b Hillier MC. Chen C.-Y. J. Org. Chem. 2006; 71: 7885
- 10c de Figueiredo RM. Frölich R. Christmann M. J. Org. Chem. 2006; 71: 4147
- 12a Sulmon P. De Kimpe N. Schamp N. Tinant B. Declercq J.-P. Tetrahedron 1988; 44: 3653
- 12b Sulmon P. De Kimpe N. Schamp N. J. Chem. Soc., Chem. Commun. 1985; 715
- 12c De Kimpe N. De Smaele D. Tetrahedron Lett. 1994; 35: 8023
- 13 Chang HO. Chul YR. Choong HY. Jin RC. Synth. Commun. 2003; 33: 4297
- 14 Sarika M. Upender KN. Synlett 2008; 108
- 15a Dejaegher Y. De Kimpe N. J. Org. Chem. 2004; 69: 5974
- 15b Brabandt WV. Dejaegher Y. Landeghem RV. De Kimpe N. Org. Lett. 2006; 8: 1101
- 16a De Kimpe N. De Smaele D. Tetrahedron 1995; 51: 5465
- 16b Salgado A. Dejaegher Y. Verniest G. Boeykens M. Gauthier C. Lopin C. Tehrani KA. De Kimpe N. Tetrahedron 2003; 59: 2231
- 17 Khan FA. Rao GH. M. Satapathy R. Parasuraman K. Org. Lett. 2007; 9: 1581
- 18 Khan FA. Prabhudas B. Dash J. Sahu N. J. Am. Chem. Soc. 2000; 122: 9558
For reviews on the synthesis and chemistry of azetidines, see: