Synthesis and structure of amino acid-derived benziodazoles: New hypervalent iodine heterocycles

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1583-1586

  Zhdankin, Viktor V ^a   Koposov, Alexey Y ^a   Su, Liansheng ^a   Boyarskikh, Vyacheslav V ^a   Netzel, Brian C ^a   Young Jr , Victor G ^b  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

^b University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALANINE; AMINO ACID; BASE; BENZAMIDE DERIVATIVE; BENZODIAZOLE; CHEMICAL COMPOUND; HETEROCYCLIC COMPOUND; IODINE; PERACETIC ACID; PHENYL GROUP; UNCLASSIFIED DRUG; VALINE;

ACIDITY; ALKALINITY; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DERIVATIZATION; OXIDATION; SYNTHESIS; X RAY ANALYSIS;

EID: 0141519200     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0344523     Document Type: Article

References (22)

1. (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997.
2. (b) Morales-Rojas, H.; Moss, R. A. Chem. Rev. 2002, 102, 2497.
3. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
4. (a) Ochiai, M.; Ito, T.; Takahashi, H.; Nakanishi, A.; Toyonari, M.; Sueda, T.; Goto, S.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 7716.
5. (b) Zhdankin, V. V. Rev. Heteroatom Chem. 1997, 17, 133.
6. (c) Muraki, T.; Togo, H.; Yokoyama, M. J. Org. Chem. 1999, 64, 2883.
7. (a) Wolf, W.; Steinberg, L. J. Chem. Soc., Chem. Commun. 1965, 449.
8. (b) Barber, H. J.; Henderson, M. A. J. Chem. Soc. C 1970, 862.
9. (c) Balthazar, T. M.; Godaz, D. E.; Stults, B. R. J. Org. Chem. 1979, 44, 1447. Naae, D. G.; Gougoutas, J. Z. J. Org. Chem. 1975, 40, 2129.
10. (c) Balthazar, T. M.; Godaz, D. E.; Stults, B. R. J. Org. Chem. 1979, 44, 1447. Naae, D. G.; Gougoutas, J. Z. J. Org. Chem. 1975, 40, 2129.
11. (d) Moss, R. A.; Chatterjee, S.; Wilk, B. J. Org. Chem. 1986, 51, 4303.
12. Zhdankin, V. V.; Arbit, R. M.; McSherry, M.; Mismash, B.; Young, V. G. J. Am. Chem. Soc. 1997, 119, 7408; Zhdankin, V. V.; Arbit, R. M.; Lynch, B. J.; Kiprof, P.; Young, V. G. J. Org. Chem. 1998, 63, 6590.
13. Zhdankin, V. V.; Arbit, R. M.; McSherry, M.; Mismash, B.; Young, V. G. J. Am. Chem. Soc. 1997, 119, 7408; Zhdankin, V. V.; Arbit, R. M.; Lynch, B. J.; Kiprof, P.; Young, V. G. J. Org. Chem. 1998, 63, 6590.
14. Zhdankin, V. V.; Koposov, A. E.; Smart, J. T.; Tykwinski, R. R.; McDonald, R.; Morales-Izquierdo, A. J. Am. Chem. Soc. 2001, 123, 4095.
15. Zhdankin, V. V.; Smart, J. T.; Zhao, P.; Kiprof, P. Tetrahedron Lett. 2000, 41, 5299.
16. 5: C, 39.92; H, 3.61; N, 3.58; I, 32.44. Found: C, 39.91; H, 3.50; N, 3.60; I, 32.21. Additional synthetic and characterization details are provided as Supporting Information.
17. (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992.
18. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
19. (c) Zhdankin, V. V.; Stang, P. J. Tetrahedron 1998, 54, 10927.
20. 2, all data). Full details on the crystal structure of 6 are available in the Supporting Information.
21. 2, all data). Full details on crystal structure of 9 are available in the Supporting Information.
22. Batchelor, R. J.; Birchall, T.; Sawyer, J. F. Inorg. Chem. 1986, 25, 1415.