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Synthesis 2016; 48(09): 1371-1380
DOI: 10.1055/s-0035-1560422
DOI: 10.1055/s-0035-1560422
paper
One-Pot Synthesis of Spirotetrahydrooxino[3,4-c]pyridines and Spirotetrahydrofuro[3,2-b]pyridin-2-ones via Lactonization from Activated Pyridyldihydroozaxoles and Bis(trimethylsilyl)ketene Acetals
Further Information
Publication History
Received: 30 November 2015
Accepted after revision: 05 February 2016
Publication Date:
01 March 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201609/lookinside/thumbnails/ss-2015-m0693-op_10-1055_s-0035-1560422-1.jpg)
Abstract
5-Methyl-2-(pyridin-3-yl)-4,5-dihydrooxazole and 5-methyl-2-(pyridin-4-yl)-4,5-dihydrooxazole activated by triflic anhydride underwent lactonization with bis(trimethylsilyl)ketene acetals to provide tetrahydrooxino[3,4-c]pyridines and tetrahydrofuro[3,2-b]pyridin-2-ones. Formation of the product was controlled by the position of the pyridyl substituent at C-3 and C-4 of the pyridyldihydrooxazole. On the other hand, 1-(trifluoromethylsulfonamido)propan-2-yl picolinate was obtained under the same conditions from 5-methyl-2-(pyridin-2-yl)-4,5-dihydrooxazole.
Key Words
lactonization - pyridyldihydrooxazoles - ketene acetals - spirotetrahydrofuro[3,2-b]pyridin-2-ones - spirotetrahydrooxino[3,4,-c]pyridinesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560422. Copies of 1H, 13C, HMBC, HSQC NMR, as well as HRMS and IR spectra for the new compounds, and X-ray data for compound 12a (CIF) are included.
- Supporting Information
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References
- 1 Beemelmanns C, Gross S, Reissig H. Chem. Eur. J. 2013; 19: 17801
- 2 Beemelmanns C, Lentz D, Reissig H. Chem. Eur. J. 2011; 17: 9720
- 3 Sarma PV. V. S, Cook JM. Org. Lett. 2006; 8: 1017
- 4 Wee AG. H, Fan G, Bayirinoba HM. J. Org. Chem. 2009; 74: 8261
- 5 Wee AG. H, Fan G. Org. Lett. 2008; 10: 17, 3869
- 6 Fan G, Wang Z, Wee AG. H. Chem. Commun. 2006; 3732
- 7 Annadi K, Wee AG. H. J. Org. Chem. 2015; 80: 5236
- 8a Satoh N, Akiba T, Yokoshima S, Fukuyama T. Angew. Chem. Int. Ed. 2007; 46: 5734
- 8b Satoh N, Akiba T, Yokoshima S, Fukuyama T. Tetrahedron 2009; 65: 3239
- 9 Wang Y, Ready JM. Org. Lett. 2012; 14: 2308
- 10 López-Reyes ME, López-Cortés JG, Ortega-Alfaro MC, Toscano RA, Alvarez-Toledano C. Tetrahedron 2013; 69: 7365
- 11 Rivera-Hernández A, Chans GM, Rudler H, López-Cortés JG, Toscano RA, Álvarez-Toledano C. Tetrahedron 2014; 70: 1861
- 12 Rivera-Hernández A, López-Jimeno IS, Carmona-Reyes GA, Alfredo-Toscano R, Penieres-Carrillo JG, Álvarez-Toledano C. Tetrahedron Lett. 2015; 56: 4829
- 13 Alvarado-Beltrán I, Maerten E, Toscano RA, López-Cortés JG, Baceiredo A, Álvarez-Toledano C. Tetrahedron: Asymmetry 2015; 26: 802
- 14 Bailey WJ, Katsuki H. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1973; 14: 1169
- 15 Takata T, Endo T. Prog. Polym. Sci. 1993; 18: 839
- 16 Hino T, Endo T. Macromolecules 2003; 36: 5902
- 17 Rokicki G. Prog. Polym. Sci. 2000; 25: 259
- 18 Endo T, Bailey W. J. Polym. Sci., Polym. Chem. Ed. 1976; 14: 1735
- 19 Thompson VP, Williams EF, Bailey WJ. J. Dent. Res. 1979; 58: 1522
- 20 Sakai S, Kobayashi Y, Itoh K, Ishii Y. J. Org. Chem. 1971; 36: 1176
- 21 Endo T, Okawara M. Synthesis 1984; 837
- 22 Stansbury JW. J. Dent. Res. 1992; 71: 1408
- 23 Shibuya I, Gama Y, Shimizu M. Heterocycles 1998; 48: 461
- 24 Rahimizadeh M, Shiri A, Bakavoli M. Chin. Chem. Lett. 2007; 18: 689
- 25 Wasserman HH, Pickett JE, Vinnick FS. Heterocycles 1981; 15: 1069
- 26 All the bis(trimethylsilyl)ketene acetals employed were prepared according the procedure reported by: Ainsworth C, Kuo Y.-N. J. Organomet. Chem. 1972; 46: 73
- 27 Aldoshin SM, Atovmyan LO, Kozina OA. Izv. Akad. Nauk SSSR, Ser. Khim. 1987; 36: 167
- 28 Aldoshin SM, Chuev II, Filipenko OS, Utenyshev AN, Lokshin V, Laregenie P, Samat A, Guglielmetti R. Russ. Chem. Bull. 1998; 47: 1089
- 29 Lide DR. Handbook of Chemistry and Physics . CRC Press; Boston: 2000
- 30 Rudler H, Denise B, Xu Y, Parlier A, Vaissermann J. Eur. J. Org. Chem. 2005; 3724
- 31 Gualo-Soberanes N, Ortega-Alfaro MC, Lopez-Cortes JG, Toscano RA, Rudler H, Alvarez-Toledano C. Tetrahedron Lett. 2010; 51: 3186
- 32 Fascione MA, Adshead SJ, Mandal PK, Kilner CA, Leach AG, Turnbull WB. Chem. Eur. J. 2012; 18: 2987
- 33 Bremberg U, Rahm F, Moberg C. Tetrahedron: Asymmetry 1998; 9: 3437