2,4-Dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5831-5834

  Fukuyama, Tohru ^a   Cheung, Mui ^b   Jow, Chung Kuang ^b   Hidai, Yuko ^a   Kan, Toshiyuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BENZENESULFONAMIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0342894825     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01334-8     Document Type: Article

References (9)

1. For a general synthesis of amines, see: Sandler, S. R.; Karo, W. Organic Functional Group Preparations, 2nd ed.; Academic, New York, 1983; Chapter 13.
2. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6374.
3. (a) Mitsunobu, O. Synthesis 1981, 1-28.
4. (b) Hughes, D. L. Org. React. 1992, 42, 335-656.
5. While a variety of amine and thiol nucleophiles can be used for the deprotection of 2,4-dinitrobenzenesulfonamides, n-propylamine was chosen because it is easy to remove (b.p. 48 °C) and inexpensive.
6. Somewhat lower yields of sulfonamides 2 were obtained using triethylamine as a base because of the concomitant decomposition of 2 via the intramolecular Meisenheimer complex. (formula presented)
7. (a) Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586-1587.
8. (b) Miller, S. C.; Scanlan, T. S. J. Am. Chem. Soc. 1997, 119, 2301-2302.
9. (c) Private communications from Drs. John Nuss (Chiron) and Lihu Yang (Merck).