Air oxidation of N-cyclopropylanilines

Synthetic Communications

Volumn 42, Issue 12, 2012, Pages 1855-1863

  Blackburn, Anthony ^a   Bowles, Daniel M ^a   Curran, Timothy T ^a   Kim, Hui ^a  

^a PFIZER INC   (United States)

Author keywords

Air oxidation; Cyclopropyl aniline; Fragmentation; Rearrangement

Indexed keywords

ACETAMIDE DERIVATIVE; ALKANE DERIVATIVE; ANILINE DERIVATIVE; PROPIONAMIDE DERIVATIVE;

ARTICLE; FRAGMENTATION REACTION; LIGHT; OXIDATION; WARMING;

EID: 84863173716     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.545166     Document Type: Article

References (30)

1. Kulinkovich, O.G.; de Meijere, A. n-Dicarbanionic titanium intermediates from monocarbanionic organometallics and their application in organic synthesis. Chem. Rev. 2000, 100, 2789-2834.
2. (a) Hanzlik, R.P.; Harriman, S. P.; Shaffer, C. L.; Koen, Y. M.; Totah, R. A.; Cerny, M. A. Synthesis and Applications of Isotopically Labelled Compounds; D. C. Dean, C. N. Filer, K. E. McCarthy, (Eds.); John Wiley & Sons: New York, 2004; vol. 8; pp. 111-114;
3. (b) Shaffer, C. L.; Morton, M. D.; Hanzlik, R. P. Enzymatic N-dealkylation of an N-cyclopropylamine: An unusual fate for the cyclopropyl group. J. Am. Chem. Soc. 2001, 123, 349-350; (Pubitemid 32062181)
4. (c) Dinnocenzo, J. P.; Karki, S. B.; Jones, J. P. On isotope effects for the cytochrom P-450 oxidation of substituted N,N-dimethylanilines. J. Am. Chem. Soc. 1993, 115, 7111-7116;
5. (d) Karki, S. B.; Dinnocenzo, J. P.; Jones, J. P.; Korzekwa, K. R. Mechanism of oxidative amine dealkylation of substituted N,N-dimethylanilines by cytochrome P-450: Application of isotope effect profiles. J. Am. Chem. Soc. 1995, 117, 3657-3664.
6. (a) Lee, J.; Sun, U. J.; Blackstock, S. C.; Cha, J. K. Facile ring opening of tertiary aminocyclopropanes by photooxidation. J. Am. Chem. Soc. 1997, 119, 10241-10242; (Pubitemid 27479944)
7. (b) Ha, J. D.; Lee, J.; Blackstock, S. C.; Cha, J. K. Intramolecular [3+2] annulation of olefin-tethered cyclopropylamines. J. Org. Chem. 1998, 63, 8510-8514. (Pubitemid 28532909)
8. Gillaspy, M. L.; Lefker, B. A.; Hada, W. A.; Hoover, D. J. A simple method for the formation of cyclopropylamines: The first synthesis of tricyclopropylamine. Tetrahedron Lett. 1995, 36, 7399-7402
9. Yoshida, Y.; Umezu, K.; Hamada, Y.; Atsumi, N.; Tabuchi, F. Practical synthesis of N-cyclopropylanilines via direct condensation of anilines with [(1-ethoxycyclopropyl)oxy]-trimethylsilane. Synlett 2003, 14, 2139-2142. (Pubitemid 37430781)
10. Vaidyanathan, G.; Wilson, J. W. Reaction of cyclopropanamines with hypochlorite. J. Org. Chem. 1989, 54, 1815-1820.
11. Wimalasena, K.; Wickman, H. B.; Mahindaratne, M. P. D. Autocatalytic radical ring opening of N-cycloproopyl-N-phenylamines under aerobic conditions-exclusive formation of the unknown oxygen adducts, N-(1,2-dioxolan-3-yl)-N-phenylamines. Eur. J. Org. Chem. 2001, 3811-3817. (Pubitemid 32983144)
12. Rynbrandt, R. H.; Dutton, F. E. Cleavage of a cyclopropane ring by singlet oxygen. J. Org. Chem. 1975, 40, 3079-3081.
13. Hiyama, T.; Koide, H.; Nozaki, H. Oxidation of cyclopropylamines and 2-phenylaziridine with lead tetraacetate. Tetrahedron Lett. 1973, 24, 2143-2144.
14. Itoh, T.; Kaneda, K.; Teranishi, S. Novel oxygenolysis of cyclopropylamines to epoxy ketones. Tetrahedron Lett. 1975, 32, 2801-2804.
15. Cui, W.; Loeppky, R. N. The synthesis of N-arylcyclopropylamines via palladiumcatalyzed C-N bond formation. Tetrahedron 2001, 57, 2953-2956. (Pubitemid 32322480)
16. Joullie and Faler reported the facile fragmentation of hydroxyphenyl-N-N-dimethylcyclopropylamine and suggested that the fragmentation was likely due to oxygen and water during purification. See Faler, C. A.; Joullie, M. M. The Kulinkovich reaction in the synthesis of constrained N,N-dialkyl neurotransmitter analogues. Org. Lett. 2007, 9, 1987-1990.
17. A large variety of N-alkyl-cyclopropylanilines are commercially available. For selected additional examples of stable N-alkyl- cyclopropylanilines in the literature, see (a) Satoh, T.; Miura, M.; Sakai, K.; Yokoyama, Y. Reaction of magnesium cyclopropylidene with N-lithio arylamines: A method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles. Tetrahedron 2006, 62, 4253-4261;
18. (b) Kang, J.; Kim, K. S. N-Cyclopropylation of aromatic amines. J. Chem. Soc. Chem. Commun. 1987, 12, 897-898;
19. (c) Bénard, S.; Neuville, L.; Zhu, J. Copper-promoted N-cyclopropylation of anilines and amines by cyclopropylboronic acid. Chem. Commun. 2010, 46, 3393-3395.
20. 2 oxidation of tertiary amines under more rigorous conditions has been reported: Riley, D. P.; Correa, P. E. An unprecedented selective autoxidation of tertiary amines to amine oxides. J. Org. Chem. 1985, 50, 1563-1564.
21. The "very fast" opening of the cyclopropane ring system has been reported. (a) Maeda, Y.; Ingold, K. U. Kinetic applications of electron paramagnetic resonance spectroscopy. 35. The search for a dialkylaminyl rearrangement: Ring opening of N-cyclobutyl-N-n-propylaminyl. J. Am. Chem. Soc. 1980, 102, 328-331;
22. (b) Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. A kinetic scale for dialkylaminyl radical reactions. J. Am. Chem. Soc. 1996, 118, 3862-3868. (Pubitemid 26164882)
23. (a) Schreiber, S. L. Hydrogen transfer from tertiary amines to trifluoroacetic anhydride. Tetrahedron Lett. 1980, 21, 1027-1030;
24. (b) Dinnocenzo, J. P.; Banach, T. E. Deprotonation of tertiary amine cation radicals: A direct experimental approach. J. Am. Chem. Soc. 1989, 111, 8646;
25. (c) Zhang, X.; Yeh, S. R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, Mariano P. S. Dynamics of α-CH deprotonation and α-desilylation reactions of tertiary amine cation radicals. J. Am. Chem. Soc. 1994, 116, 4211-4220; (Pubitemid 24978386)
26. (d) Loeppky, R. N.; Singh, S. P.; Elomari, S.; Hastings, R.; Theiss, T. E. Evidence for radical cations in linked mechanisms of N,N-dialkyl aromatic amine nitration and nitrosative dealkylation. J. Am. Chem. Soc. 1998, 120, 5193-5202. (Pubitemid 28328882)
27. Antibacterial Quinolones and Their Preparations. Otsuka Pharmaceutical Co., Ltd.: Japan. NL 8700471, September 16, 1987.
28. Fifolt, M. J.; Sojka, S. A.; Wolfe, R. A.; Hojnicki, D. S.; Bieron, J. F.; Dinan, F. J. A chemical shift additivity method for the prediction of fluorine-19 chemical shifts in fluoroaromatic compounds. JOC 1989, 54(13), 3019-3023.
29. Bradley, G.; Clark, J.; Kernick, W. 2,3-Dihydroquinolin-4(1H)-ones. Part I. Halogen-substituted 2,3-dihydroquinolin-4(1H)-ones and their 1-(2-acylethyl) derivatives. J. Chem. Soc., Perkin Trans. 1 1972, 16, 2019-2023.
30. Kajihara, K.; Arisaua, M.; Shuto, S. A method for cleaving an allyl protecting group at the amid nitrogen of peptides by one-pot olefin isomerization-oxidation. JOC 2008, 73(23), 9494-9496.