An efficient and novel method for the synthesis of arylsulfonamides and sulfonic acid esters under solvent-free conditions

Sulfur Letters

Volumn 24, Issue 3, 2000, Pages 137-145

  Hajipour, Abdol R ^a   Mallakpour, Shadpour E ^a   Najafi, Ali R ^a   Mazlumi, Gh ^a  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

DABCO; Solid state; Sulfonamides; Sulfonic esters; Sulfonyl chlorides

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; CHLORIDE; ESTER DERIVATIVE; SOLVENT; SULFONAMIDE;

ARTICLE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034586895     PISSN: 02786117     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. a) D. Lendnicer and L. A. Mitscher, The Organic Chemistry of Drugs Synthesis, Wiley, New York, 1977, Vol 1, pp 120-132.; 1980, Vol 2, pp 112-119.
2. a) D. Lendnicer and L. A. Mitscher, The Organic Chemistry of Drugs Synthesis, Wiley, New York, 1977, Vol 1, pp 120-132.; 1980, Vol 2, pp 112-119.
3. b) B. Raju, C. Wu, A. Kois, E. J. Verner, R. Castillo, I.; Okun, F. D. Stavors and M. F. Chan, Bioorg. Med. Chem. Lett., 6, 2651 (1996).
4. c) H. Yoshino, N. Veda Niijima, H. Sugumi, Y. Kotake, N. Koyanagi, K. Yoshimatsu, M. Asada, T. Watanabe, T. Nagasu, K. Tsukahara, A. Lijima and K. J. Kitch, Med. Chem. 35, 2496 (1992).
5. d) J. W. Ellingobe, M. W. Winkley, T. T. Nguyen, A. Parsons, H. Pletsch, Rehwinkel. and R. Scheyer, Bioorg. Med. Chem. Lett., 5, 1219 (1996).
6. A. M. Fivush and T. M. Willson, Tetrahedron Lett., 38, 7151 (1997).
7. B. Raju and T. P. Kogan, Tetrahedron Lett., 38, 3373 (1997).
8. W. A. Gensler, F. J. Frank, S. K. Dheer and J. W. Lauher, J. Org. Chem., 36, 4102 (1971).
9. I. B. Douglass and R. V. Nuton, J. Org. Chem., 33, 2104 (1968).
10. J. H. Youn and R. Herrmann, Synthesis, 72 (1987).
11. G. Barm, A. Loupy, M. Majdoub, E. Gutierrez and E. Ruiz-Hitzky, Tetrahedron, 46, 5167 (1990).
12. A. R. Hajipour, I. Mohammadpoor-Baltork, K. Nikbaghat and H. Imanzadeh Synth. Commun., 29, 1697 (1999).
13. A. R. Hajipour, S. E. Mallakpour and H. Imanzadeh, J. Chem. Research (S), 228 (1999).
14. A. R. Hajipour, S. E. Mallakpour and H. Imanzadeh, Chem Lett, 99 (1999).
15. A. R. Hajipour, Indian. J. Chem., 36B, 1069 (1997).
16. A. R. Hajipour, S. E. Mallakpour and A. Afrousheh, Tetrahedron, 55, 231 (1999).
17. a) P. C. Bulman Page, R. D. Wilkes, D. Reynolds, Alkyl Chalcogenides: Sulfur-based Functional Groups. In Comprehensive Organic Functional Group Transformations: A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Eds., Pergamon. Cambridge, Vol. 2, pp 194-202 (1995).
18. b) P. C. Taylor, Vinyl and Aryl Chalcogenides: Sulfur, Selenium and Tellurium-based Functional Groups. In Comprehensive Organic Functional Group Transformations: A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Eds., Pergamon. Cambridge, Vol. 2, p 720 (1995).
19. c) J. Mulzer, Carboxylic Esters and Lactones, Functional Groups. In Comprehensive Organic Functional Group Transformations: A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Eds., Pergamon. Cambridge, Vol. 5, pp 121-179 (1995).
20. a) A. Schöberl; A. Wagner,. Herstellung von Sulfensäureestern. In Houben-Weyl, Methoden der Organischen Chemie; Müller, E., Ed.; Vol 9, Schwefel, Selen, Tellurverbindungen, 4th ed., Thieme: Stuttgart; pp 267-283 (1955).
21. b) R. Schubart, Sulfensäureorganoester aus Sulfensäurehalogeniden. In Houben-Weyl, Methoden der Organischen Chemie; Klamann, D., Ed.; Vol Ell, Organische Schwefel-Verbindungen 1, 4th ed.; Thieme: Stuttgart; pp 101-104 (1985).
22. c) F. Muth, Sulfonsäure-Ester aus Sulfonylhalogeniden. In Houben-Weyl, Methoden der Organischen Chemie; Mller, E., Ed.; Vol 9, Schwefel-, Selen-, Tellur-Verbindungen, 4th ed.; Thieme: Stuttgart; pp 665-670 (1955).
23. d) S. Pawlenko, Arylsulfonsäuren. In Houben-Weyl, Methoden der Organischen Chemie; Klamann, D., Ed.; Vol E11, Organische Schwefel-Verbindungen 11, 4th ed.; Thieme: Stuttgart, pp 1090-1092 (1985).
24. e) H. Pielartzik, B. Irmisch-Pielartzik, T. Eicher, Offenkettige Carbonsäureester aus Carbonsäurechloriden und Alkoholen. In Houben-Weyl, Methoden der Organischen Chemie; Falbe, J., Ed.; Vol E5, Carbonsuren und Carbonsure-Derivate 1, 4th ed.; Thieme: Stuttgart; pp 695-698 (1985).
25. a) G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem., 90, 602 (1978) and Angew. Chem., Int. Ed. Engl, 17, 569 (1978)
26. a) G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem., 90, 602 (1978) and Angew. Chem., Int. Ed. Engl, 17, 569 (1978)
27. b) G. Höfle, W. Steglich, Synthesis, 619 (1973).
28. a) W. G. Kabalka, M. Varma, R. S. Varma, J. Org. Chem., 51, 2386 (1986)
29. b) L.F. Fieser, M. Fieser, Reagents in Organic Synthesis; Wiley: New York; p 1180 (1967).
30. a) References cited in March, J., Advanced Organic Chemistry, 4th ed.; Wiley: New York; p 722 (1992)
31. b) J. Hoyle, Preparation of Sulfonic Acids, Esters, Amides and Halides. In The Chemistry of Sulfonic Acids, Esters and their Derivatives; Patai, S.; Rappoport, Z., Eds.; Wiley: New York; pp 366-379 (1991).
32. F. F. V. Scriven, Reactivity of Pyridines and Their Benzo Derivatives; Reactivity at Ring Atoms, In Comprehensive Heterocyclic Chemistry, Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford; Vol. 2, pp 166-313 (1994)
33. J. Hartung, S. Hunig, R. Kneuer, M. Schwarz, H. Wenner, Synthesis, 1433 (1997).
34. Aldrich Catalog, Handbook of Fine Chemicals, 1990-91.