메뉴 건너뛰기




Volumn 36, Issue 1, 1999, Pages 161-175

Fused 1,2-dithioles. IV. Synthesis and reactions of 1,2-dithiole S- oxides

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DITHIOLE OXIDE; 1,2 DITHIOLOPYRROLONE; ANTIBIOTIC AGENT; DIMETHYL 4 METHYL 2,5,5 TRIOXO 4H 2LAMBDA4,5LAMBDA6 1,2 DITHIOLO[4,3 C][1,2]THIAZOLE 3,6 DICARBOXYLIC ACID; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032938029     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570360125     Document Type: Article
Times cited : (13)

References (88)
  • 11
    • 13044261731 scopus 로고
    • Part of the Ph. D. Dissertation Universität München, Germany, details to be published elsewhere
    • Part of the Ph. D. Dissertation of E. Immerz-Winkler, Universität München, Germany, 1981; details to be published elsewhere.
    • (1981)
    • Immerz-Winkler, E.1
  • 12
    • 0027293979 scopus 로고
    • E. Jucker, ed, Birkhäuser, Basel
    • [a] E. J. Lien, in Progress in Drug Research, Vol 40, E. Jucker, ed, Birkhäuser, Basel, 1993, p 163;
    • (1993) Progress in Drug Research , vol.40 , pp. 163
    • Lien, E.J.1
  • 13
    • 0025995750 scopus 로고
    • E. Jucker, ed, Birkhäuser, Basel
    • [b] A. Burger, in Progress in Drug Research, Vol 37, E. Jucker, ed, Birkhäuser, Basel, 1991, p 287.
    • (1991) Progress in Drug Research , vol.37 , pp. 287
    • Burger, A.1
  • 14
    • 0017804434 scopus 로고
    • Metabolism of dithioles by mitochondrial cytochrom P450 oxidation to furnish thiosulphinates is well known, see: D. Fukushima, Y. H. Kim, T. Iyanagi and S. Oae, J. Biochem., 83, 1019 (1978).
    • (1978) J. Biochem. , vol.83 , pp. 1019
    • Fukushima, D.1    Kim, Y.H.2    Iyanagi, T.3    Oae, S.4
  • 15
    • 13044302231 scopus 로고    scopus 로고
    • M. E. Wolff, ed, John Wiley & Sons, New York
    • In contrast, saturated 1,2-dithiolanes such as the physiologically important α-lipoic acid are easily attacked by nucleophiles without preceeding S-oxidation. For details, see: J. D. Adams Jr., in Burger's Medicinal Chemistry and Drug Discovery, Vol 3, M. E. Wolff, ed, John Wiley & Sons, New York, 1996, p 308.
    • (1996) Burger's Medicinal Chemistry and Drug Discovery , vol.3 , pp. 308
    • Adams Jr., J.D.1
  • 21
    • 13044301613 scopus 로고    scopus 로고
    • Research Code No. 240944, Prous Science, Barcelona
    • [a] Annu. Drug. Data Rep., 19, 149; Research Code No. 240944, J. R. Prous, ed, Prous Science, Barcelona, 1997;
    • (1997) Annu. Drug. Data Rep. , vol.19 , pp. 149
    • Prous, J.R.1
  • 26
    • 0039996906 scopus 로고
    • P. L. Folkins and D. N. Harpp, J. Org. Chem., 56, 904 (1991). In the case of oxidation of dithiole 5a, however, even less than equimolar amounts of m-chloroperbenzoic acid gave monoxide 6a accompanied by about 5% of its dioxide 7.
    • (1991) J. Org. Chem. , vol.56 , pp. 904
    • Folkins, P.L.1    Harpp, D.N.2
  • 27
    • 0842341771 scopus 로고
    • Calculations employing AM1 software and GAUSSIAN 94 ab initio-methods indicated that S(2) is the far more electron-rich sulphur atom, for further details, see: [a] M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985); [b] GAUSSIAN 94; [c] N. C. Cohen and V. Tschinke, in Drug Research, Vol 45, E. Jucker, ed, Birkhäuser, Basel, 1995, p 205.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.J.P.4
  • 28
    • 0004133516 scopus 로고    scopus 로고
    • Calculations employing AM1 software and GAUSSIAN 94 ab initio-methods indicated that S(2) is the far more electron-rich sulphur atom, for further details, see: [a] M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985); [b] GAUSSIAN 94; [c] N. C. Cohen and V. Tschinke, in Drug Research, Vol 45, E. Jucker, ed, Birkhäuser, Basel, 1995, p 205.
    • GAUSSIAN 94
  • 29
    • 0028867884 scopus 로고
    • E. Jucker, ed, Birkhäuser, Basel
    • Calculations employing AM1 software and GAUSSIAN 94 ab initio-methods indicated that S(2) is the far more electron-rich sulphur atom, for further details, see: [a] M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985); [b] GAUSSIAN 94; [c] N. C. Cohen and V. Tschinke, in Drug Research, Vol 45, E. Jucker, ed, Birkhäuser, Basel, 1995, p 205.
    • (1995) Drug Research , vol.45 , pp. 205
    • Cohen, N.C.1    Tschinke, V.2
  • 30
  • 31
    • 13044303499 scopus 로고    scopus 로고
    • note
    • Complete details of the structure investigations are available on request from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England, on quoting the names of the authors, the compound number and the journal citation.
  • 34
    • 0009315824 scopus 로고
    • Sodium periodate/iodine: [a] Y. H. Kim, T. Takata and S. Oae, Tetrahedron Letters, 2305 (1978); [b] T. Takata, Y. H. Kim and S. Oae, Bull. Chem. Soc., Japan, 54, 1443 (1981).
    • (1978) Tetrahedron Letters , pp. 2305
    • Kim, Y.H.1    Takata, T.2    Oae, S.3
  • 35
    • 0011763468 scopus 로고
    • Sodium periodate/iodine: [a] Y. H. Kim, T. Takata and S. Oae, Tetrahedron Letters, 2305 (1978); [b] T. Takata, Y. H. Kim and S. Oae, Bull. Chem. Soc., Japan, 54, 1443 (1981).
    • (1981) Bull. Chem. Soc., Japan , vol.54 , pp. 1443
    • Takata, T.1    Kim, Y.H.2    Oae, S.3
  • 42
    • 0001252037 scopus 로고
    • P. L. Folkins and D. N. Harpp, J. Am. Chem. Soc., 113, 8998 (1991); see also: P. L. Folkins and D. N. Harpp, J. Am. Chem. Soc., 115, 3066 (1993).
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8998
    • Folkins, P.L.1    Harpp, D.N.2
  • 43
    • 0000265334 scopus 로고
    • P. L. Folkins and D. N. Harpp, J. Am. Chem. Soc., 113, 8998 (1991); see also: P. L. Folkins and D. N. Harpp, J. Am. Chem. Soc., 115, 3066 (1993).
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3066
    • Folkins, P.L.1    Harpp, D.N.2
  • 46
    • 0342947902 scopus 로고
    • A thorough literature search revealed only one report of the use of 1,2-dimethylhydrazine as a reductant in the case of diaziridinones; F. D. Greene, W. R. Bergmark and J. G. Pacifici, J. Org. Chem., 34, 2263 (1969).
    • (1969) J. Org. Chem. , vol.34 , pp. 2263
    • Greene, F.D.1    Bergmark, W.R.2    Pacifici, J.G.3
  • 47
    • 3643104448 scopus 로고
    • The reduction of thiamine disulphide monoxide was reported by G. Tsukamoto, T. Watanabe and I. Utsumi, Bull. Chem. Soc., Japan, 42, 2566 (1969). In accordance with the results reported therein we obtained a near instantaneous reaction of thiosulphinate esters 6a and 15b with thiophenol, whereas reduction with 1-propanethiol required days for completion; see also T. Takata and T. Endo, ref [23], p 566.
    • (1969) Bull. Chem. Soc., Japan , vol.42 , pp. 2566
    • Tsukamoto, G.1    Watanabe, T.2    Utsumi, I.3
  • 48
    • 13044314264 scopus 로고    scopus 로고
    • ref [23], p 566
    • The reduction of thiamine disulphide monoxide was reported by G. Tsukamoto, T. Watanabe and I. Utsumi, Bull. Chem. Soc., Japan, 42, 2566 (1969). In accordance with the results reported therein we obtained a near instantaneous reaction of thiosulphinate esters 6a and 15b with thiophenol, whereas reduction with 1-propanethiol required days for completion; see also T. Takata and T. Endo, ref [23], p 566.
    • Takata, T.1    Endo, T.2
  • 49
    • 0009481491 scopus 로고
    • Other thiosulphinates were reported to undergo thiolysis upon treatment with mercaptans, e.g. [a] L. Field and R. B. Barbee, J. Org. Chem., 34, 1792 (1969); [b] L. Field and P. M. Giles Jr., J. Org. Chem., 36, 309 (1971).
    • (1969) J. Org. Chem. , vol.34 , pp. 1792
    • Field, L.1    Barbee, R.B.2
  • 50
    • 0011027730 scopus 로고
    • Other thiosulphinates were reported to undergo thiolysis upon treatment with mercaptans, e.g. [a] L. Field and R. B. Barbee, J. Org. Chem., 34, 1792 (1969); [b] L. Field and P. M. Giles Jr., J. Org. Chem., 36, 309 (1971).
    • (1971) J. Org. Chem. , vol.36 , pp. 309
    • Field, L.1    Giles Jr., P.M.2
  • 51
    • 0008870044 scopus 로고
    • Georg Thieme, Stuttgart
    • Receent reviews of the chemistry of sulphenamides are [a] R. Schubart, in Houben-Weyl Methoden der organischen Chemie, Vol E11, Georg Thieme, Stuttgart, 1985, p 107; [b] L. Craine and M. Raban, Chem. Rev., 89, 689 (1989); [c] J. Drabowicz, P. Kielbasinski and M. Mikolajczyk, in The Chemistry of Sulphenic Acids and their Derivatives, S. Patai, ed, John Wiley & Sons, New York, 1990, p 221.
    • (1985) Houben-Weyl Methoden der Organischen Chemie , vol.E11 , pp. 107
    • Schubart, R.1
  • 52
    • 33845183598 scopus 로고
    • Receent reviews of the chemistry of sulphenamides are [a] R. Schubart, in Houben-Weyl Methoden der organischen Chemie, Vol E11, Georg Thieme, Stuttgart, 1985, p 107; [b] L. Craine and M. Raban, Chem. Rev., 89, 689 (1989); [c] J. Drabowicz, P. Kielbasinski and M. Mikolajczyk, in The Chemistry of Sulphenic Acids and their Derivatives, S. Patai, ed, John Wiley & Sons, New York, 1990, p 221.
    • (1989) Chem. Rev. , vol.89 , pp. 689
    • Craine, L.1    Raban, M.2
  • 53
    • 0003649925 scopus 로고
    • S. Patai, ed, John Wiley & Sons, New York
    • Receent reviews of the chemistry of sulphenamides are [a] R. Schubart, in Houben-Weyl Methoden der organischen Chemie, Vol E11, Georg Thieme, Stuttgart, 1985, p 107; [b] L. Craine and M. Raban, Chem. Rev., 89, 689 (1989); [c] J. Drabowicz, P. Kielbasinski and M. Mikolajczyk, in The Chemistry of Sulphenic Acids and their Derivatives, S. Patai, ed, John Wiley & Sons, New York, 1990, p 221.
    • (1990) The Chemistry of Sulphenic Acids and Their Derivatives , pp. 221
    • Drabowicz, J.1    Kielbasinski, P.2    Mikolajczyk, M.3
  • 54
    • 13044299467 scopus 로고    scopus 로고
    • Part of the Ph. D. Dissertation Universität München, Germany, details to be published elsewhere
    • Part of the Ph. D. Dissertation of T. Luchterhandt, Universität München, Germany, 1998; details to be published elsewhere.
    • (1998)
    • Luchterhandt, T.1
  • 55
    • 0002594745 scopus 로고
    • Reductions of sulphinamides to sulphenamides with thionyl chloride or tributylphosphane have previously been reported; [a] G. Kresze, C. Seyfried and A. Trede, Liebigs Ann. Chem., 715, 223 (1962); [b] N. Finch, S. Ricca Jr. and L. H. Werner, J. Org. Chem., 45, 3416 (1980).
    • (1962) Liebigs Ann. Chem. , vol.715 , pp. 223
    • Kresze, G.1    Seyfried, C.2    Trede, A.3
  • 56
    • 0019124893 scopus 로고
    • Reductions of sulphinamides to sulphenamides with thionyl chloride or tributylphosphane have previously been reported; [a] G. Kresze, C. Seyfried and A. Trede, Liebigs Ann. Chem., 715, 223 (1962); [b] N. Finch, S. Ricca Jr. and L. H. Werner, J. Org. Chem., 45, 3416 (1980).
    • (1980) J. Org. Chem. , vol.45 , pp. 3416
    • Finch, N.1    Ricca Jr., S.2    Werner, L.H.3
  • 57
    • 13044315319 scopus 로고    scopus 로고
    • in ref [23], p 339
    • S. Braverman, in ref [23], p 339.
    • Braverman, S.1
  • 58
  • 61
    • 33847805414 scopus 로고    scopus 로고
    • E. Blockand J. O'Connor, J. Am. Chem. Soc., 96, 3921 (1974) and ibidem 3929.
    • J. Am. Chem. Soc. , pp. 3929
  • 65
    • 0003164738 scopus 로고    scopus 로고
    • S. Patai, ed, John Wiley & Sons, New York
    • For a review dealing with other formal adducts of thiols to nitroso groups, see P. Eyer and D. Galleman, in The Chemistry of Amino, Nitroso, Nitro and Related Groups, Suppl F2, S. Patai, ed, John Wiley & Sons, New York, 1996, p 999.
    • (1996) The Chemistry of Amino, Nitroso, Nitro and Related Groups , Issue.SUPPL. F2 , pp. 999
    • Eyer, P.1    Galleman, D.2
  • 66
    • 84954615220 scopus 로고
    • N-Aryl substituted hydroxylamines were previously shown to react via arylnitrenium ion intermediates with nucleobases such as guanine: [a] M. Novak and S. A. Kennedy, J. Am. Chem. Soc., 117, 574 (1995); [b] M. Famulok, F. Bosold and G. Boche, Angew. Chem., Int. Ed. Engl., 28, 337 (1988); [c] R. A. Mc Celland, M. J. Kahley and P. A. Davidse, J. Phys. Org. Chem., 9, 355 (1996).
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 574
    • Novak, M.1    Kennedy, S.A.2
  • 67
    • 84990148608 scopus 로고
    • N-Aryl substituted hydroxylamines were previously shown to react via arylnitrenium ion intermediates with nucleobases such as guanine: [a] M. Novak and S. A. Kennedy, J. Am. Chem. Soc., 117, 574 (1995); [b] M. Famulok, F. Bosold and G. Boche, Angew. Chem., Int. Ed. Engl., 28, 337 (1988); [c] R. A. Mc Celland, M. J. Kahley and P. A. Davidse, J. Phys. Org. Chem., 9, 355 (1996).
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 337
    • Famulok, M.1    Bosold, F.2    Boche, G.3
  • 68
    • 13044308460 scopus 로고    scopus 로고
    • N-Aryl substituted hydroxylamines were previously shown to react via arylnitrenium ion intermediates with nucleobases such as guanine: [a] M. Novak and S. A. Kennedy, J. Am. Chem. Soc., 117, 574 (1995); [b] M. Famulok, F. Bosold and G. Boche, Angew. Chem., Int. Ed. Engl., 28, 337 (1988); [c] R. A. Mc Celland, M. J. Kahley and P. A. Davidse, J. Phys. Org. Chem., 9, 355 (1996).
    • (1996) J. Phys. Org. Chem. , vol.9 , pp. 355
    • Mc Celland, R.A.1    Kahley, M.J.2    Davidse, P.A.3
  • 69
  • 70
    • 2642541172 scopus 로고
    • In contrast, reaction of acyclic thiosulphonate esters with amines was reported to give sulphenamides; for details, see J. E. Dunbar and J. H. Rogers, J. Org. Chem., 31, 2842 (1966).
    • (1966) J. Org. Chem. , vol.31 , pp. 2842
    • Dunbar, J.E.1    Rogers, J.H.2
  • 71
    • 13044309073 scopus 로고    scopus 로고
    • note
    • This novel selective reducing agent, however, surprisingly failed to provide the corresponding dithioles from both the dioxide 20c and the monoxide 6a.
  • 73
    • 13044261729 scopus 로고    scopus 로고
    • Part of the Ph. D. Dissertation Universität München, Germany, details to be published elsewhere
    • Compounds 28 and 29 were recently synthesized by us using an independent route; Part of the Ph. D. Dissertation of A. Windt, Universität München, Germany, 1997; details to be published elsewhere.
    • (1997)
    • Windt, A.1
  • 76
    • 13044301612 scopus 로고    scopus 로고
    • in ref [23], pp 314 and 325
    • The proposed mechanism for this ring contraction might bear some formal resemblance to known sulphinate-sulphone rearrangements; for details, see [a] S. Braverman, in ref [23], pp 314 and 325; [b] Y. Miura, Y. Nakamura and M. Kinoshita, Chem. Letters 1, 521 (1978).
    • Braverman, S.1
  • 77
    • 84942711312 scopus 로고
    • The proposed mechanism for this ring contraction might bear some formal resemblance to known sulphinate-sulphone rearrangements; for details, see [a] S. Braverman, in ref [23], pp 314 and 325; [b] Y. Miura, Y. Nakamura and M. Kinoshita, Chem. Letters 1, 521 (1978).
    • (1978) Chem. Letters , vol.1 , pp. 521
    • Miura, Y.1    Nakamura, Y.2    Kinoshita, M.3
  • 79
    • 13044315318 scopus 로고    scopus 로고
    • in ref [23], p 542
    • [b] T. Takata and T. Endo, in ref [23], p 542;
    • Takata, T.1    Endo, T.2
  • 81
    • 13044298820 scopus 로고
    • Georg Thieme, Stuttgart
    • A few representatives of the corresponding oxa analogues, the imidosulphonic acid esters, however, are known; for details see [a] S. Pawlenko, in Houben-Weyl Organische Schwefelverbindungen, Vol E11, Georg Thieme, Stuttgart, 1985, p 1125;
    • (1985) Houben-Weyl Organische Schwefelverbindungen , vol.E11 , pp. 1125
    • Pawlenko, S.1
  • 82
    • 0001649254 scopus 로고
    • N. Jones, ed, Pergamon Press, Oxford UK
    • [b] C. R. Johnson, in Comprehensive Organic Chemistry, Vol 3, N. Jones, ed, Pergamon Press, Oxford UK, 1979, p 223.
    • (1979) Comprehensive Organic Chemistry , vol.3 , pp. 223
    • Johnson, C.R.1
  • 83
    • 13044314888 scopus 로고    scopus 로고
    • Part of the Ph. D. Dissertation Universität München, Germany, details to be published elsewhere
    • Part of the Ph. D. Dissertation of T. Fuchs, Universität München, Germany, 1997; details to be published elsewhere.
    • (1997)
    • Fuchs, T.1
  • 84
    • 0004150157 scopus 로고
    • Universität Goettingen, Germany
    • G. M. Sheldrick, SHELXS-86, Universität Goettingen, Germany, 1990.
    • (1990) SHELXS-86
    • Sheldrick, G.M.1
  • 85
    • 0004150157 scopus 로고
    • Universität Goettingen, Germany
    • G. M. Sheldrick, SHELXL-93, Universität Goettingen, Germany, 1993.
    • (1993) SHELXL-93
    • Sheldrick, G.M.1
  • 86
    • 0004190368 scopus 로고
    • ZORTEP, Universität Heidelberg, Germany
    • L. Zsolnai, XPMA, ZORTEP, Universität Heidelberg, Germany, 1994.
    • (1994) XPMA
    • Zsolnai, L.1
  • 87
    • 0342917920 scopus 로고
    • Coll H. E. Baumgarten, ed, John Wiley & Sons, New York
    • H. Hart, R. M. Lange and P. M. Collins, Organic Syntheses, Coll Vol V, H. E. Baumgarten, ed, John Wiley & Sons, New York, 1973, p 598.
    • (1973) Organic Syntheses , vol.5 , pp. 598
    • Hart, H.1    Lange, R.M.2    Collins, P.M.3
  • 88
    • 13044315515 scopus 로고
    • Part of the Ph. D. Dissertation Universität München, Germany, details to be published elsewhere
    • Part of the Ph. D. Dissertation of B. Zimmer, Universität München, Germany, 1995; details to be published elsewhere.
    • (1995)
    • Zimmer, B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.