One-pot microwave-promoted synthesis of nitriles from aldehydes via tert-butanesulfinyl imines

Synthesis

Volumn , Issue 21, 2007, Pages 3385-3389

  Tanuwidjaja, Jessica ^a   Peltier, Hillary M ^a   Lewis, Jared C ^a   Schenkel, Laurie B ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Aldehydes; Microwave; Nitriles; tert butanesulfinamide; tert butanesulfinyl imine

Indexed keywords

NITRILES; TERT BUTANESULFINAMIDE; TERT-BUTANESULFINYL IMINE;

ALDEHYDES; FUNCTIONAL GROUPS; MICROWAVES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYANIDES;

2 BENZYLOXYPROPIONITRILE; 4 (ISOPROPYLOXYCARBONYL)BENZONITRILE; 4 CYANOBENZAMIDE; 4 PYRIDINECARBONITRILE; ADAMANTANE 1 CARBONITRILE; ALDEHYDE DERIVATIVE; HYDROCINNAMONITRILE; IMINE; NAPHTHALENE DERIVATIVE; NITRILE; TERT BUTANESULFINYL IMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICROWAVE RADIATION; ONE POT SYNTHESIS; SYNTHESIS; TECHNIQUE;

EID: 36448987559     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990805     Document Type: Article

References (25)

1. Mukade, T.; Dragoli, D. R.; Ellman, J. A. J. Comb. Chem. 2003, 5, 590.
2. Schenkel, L. B.; Ellman, J. A. Org. Lett. 2004, 6, 3621.
3. (a) Bandgar, B. P.; Makone, S. S. Synlett 2003, 262.
4. (b) Baxendale, I. R.; Ley, S. V.; Sneddon, H. F. Synlett 2002, 775.
5. (c) Talukdar, S.; Hsu, J.-L.; Chou, T.-C.; Fang, J.-M. Tetrahedron Lett. 2001, 42, 1103.
6. (d) Erman, M. B.; Snow, J. W.; Williams, M. J. Tetrahedron Lett. 2000, 41, 6749.
7. (a) Eshghi, H.; Gordi, Z. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 619.
8. (b) Movassagh, B.; Shokri, S. Tetrahedron Lett. 2005, 46, 6923.
9. (c) Sharghi, H.; Sarvari, M. H. Tetrahedron 2002, 58, 10323.
10. (d) Niknam, K.; Karami, B.; Kiasat, A. R. Bull. Korean Chem. Soc. 2005, 26, 975.
11. (a) For a review on tert-butanesulfinamide-based methods, see: Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
12. (b) For a general review on sulfinyl imine chemistry, see: Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869.
13. (c) For a review on the synthesis and applications of sulfinamides, see: Senanayake, C. H.; Krishnamurthy, D.; Lu, Z.-H.; Zhengxu, H.; Gallou, I. Aldrichimica Acta 2005, 38, 93.
14. (d) For a general review on additions to arenesulfinyl imines, see: Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003.
15. Hughes, T. V.; Cava, M. P. J. Org. Chem. 1999, 64, 313.
16. Blay, G.; Cardona, L.; Garcia, B.; Lahoz, L.; Pedro, J. R. Tetrahedron 1996, 52, 8611.
17. Takeuchi, K.; Kitagawa, I.; Akiyama, F.; Shibata, T.; Kato, M.; Okamoto, K. Synthesis 1987, 612.
18. Olah, G. A.; Farooq, O.; Prakash, G. K. S. Synthesis 1985, 1140.
19. Mlinaric-Majerski, K.; Margeta, R.; Veljkovic, J. Synlett 2005, 2089.
20. Lee, K.; Han, S.-B.; Yoo, E.-M.; Chung, S.-R.; Oh, H.; Hong, S. Synth. Commun. 2004, 34, 1775.
21. Meisenbach, M.; Allmendinger, T.; Mak, C.-P. Org. Process Res. Dev. 2003, 7, 553.
22. Ohashi, M.; Miyake, K.; Tsujimoto, K. Bull. Chem. Soc. Jpn. 1980, 53, 1683.
23. Adlington, R. M.; Baldwin, J. E.; Becker, G. W.; Chen, B.; Cheng, L.; Cooper, S. L.; Hermann, R. B.; Howe, T. J.; McCoull, W.; McNulty, A. M.; Neubauer, B. L.; Pritchard, G. J. J. Med. Chem. 2001, 44, 1491.
24. Enders, D.; von Berg, S.; Jandeleit, B. Org. Synth. 2004, 10, 66.
25. Cazes, B.; Julia, S. Tetrahedron 1979, 35, 2655.