RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2005(15): 2521-2526
DOI: 10.1055/s-2005-872092
DOI: 10.1055/s-2005-872092
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Acid- and Metal-Free One-Pot Synthesis of Benzothiazoles from Carboxylic Acids
Weitere Informationen
Received
7 March 2005
Publikationsdatum:
20. Juli 2005 (online)
Publikationsverlauf
Publikationsdatum:
20. Juli 2005 (online)
Abstract
Carboxylic acids are converted to benzothiazoles in a one-pot reaction with thionyl chloride followed by treatment with 2-aminothiophenol under acid- and catalyst-free conditions.
Key words
benzothiazoles - carboxylic acids - thionyl chloride - 2-aminothiophenol - acid-free - catalyst-free
-
1a
Hall IH.Peaty NJ.Henry JR.Easmon J.Heinisch G.Purstinger G. Arch. Pharm. (Weinheim) 1999, 332: 115 -
1b
Bénéteau V.Besson T.Guillard J.Léonce S.Pfeiffer B. Eur. J. Med. Chem. 1999, 34: 1053 -
1c
Hutchinson I.Bradshaw TD.Matthews Stevens MFG.Westwell AD. Bioorg. Med. Chem. Lett. 2003, 13: 471 ; and the references cited therein - 2
Palmer PJ.Trigg RB.Warrington JV. J. Med. Chem. 1971, 14: 248 -
3a
Benazzouz A.Boraud T.Dubédat P.Boireau A.Stutzmann J.-M.Gross C. Eur. J. Pharmacol. 1995, 284: 299 -
3b
Jimonet P.Audiau F.Barreau M.Blanchard J.-C.Boireau A.Bour Y.Coléno M.-A.Doble A.Doerflinger G.Huu CD.Donat M.-H.Duchesne JM.Ganil P.Guérémy C.Honoré E.Just B.Kerphirique R.Gontier S.Hubert P.Laduron PM.Blevec JL.Meunier M.Miquet J.-M.Nemecek C.Pasquet M.Piot O.Pratt J.Rataud J.Reibaud M.Stutzmann J.-M.Mignani S. J. Med. Chem. 1999, 42: 2828 - 4
Lara B.Gandia L.Tores A.Martinez-Sierra R.Garcia AG.Lopez MG. Eur. J. Pharmacol. 1997, 325: 109 -
5a
Mylari BL.Larson ER.Beyer TA.Zembrowski WJ.Aldinger CE.Dee MF.Siegel TW.Singleton DH. J. Med. Chem. 1991, 34: 108 -
5b
Kotani T.Nagaki Y.Ishii A.Konishi Y.Yago H.Suehiro S.Okukado N.Okamoto K. J. Med. Chem. 1997, 40: 684 -
6a
Sato G.Chimoto T.Aoki T.Hosokawa S.Sumigama S.Tsukidate K.Sagami F. J. Toxicol. Sci. 1999, 24: 165 -
6b
Naitoh T.Kawaguchi S.Kakiki M.Ohe H.Kajiwara A.Horie T. Xenobiotica 1998, 28: 269 -
6c
Kagaya T.Kajiwara A.Nagato S.Akasaka K.Kubota A. J. Pharmacol. Exp. Ther. 1996, 278: 243 -
7a
Hadjipavlou-Litina DJ.Geronikaki AA. Drug Des. Discov. 1997, 15: 199 -
7b
Oketani K.Inoue T.Murakami M. Eur. J. Pharmacol. 2001, 427: 159 - 8
Paramashivappa R.Phani Kumar P.Subba Rao PV.Srinivasa Rao A. Bioorg. Med. Chem. Lett. 2003, 13: 657 - 9
Nagel AA.Liston DR.Jung S.Mahar M.Vincent LA.Chapin D.Chen YL.Hubbard S.Ives JL.Jones SB. J. Med. Chem. 1995, 38: 1084 - 10
Matthews JH.Krishnan R.Costanzo MJ.Maryanoff BE.Tulinsky A. Biophys. J. 1996, 2830 - 11
Caccese RG.DiJoseph JF.Scotnicki JS.Borella LE.Adams LM. Agents Actions 1991, 34: 223 - 12
Sohn SK.Chang MS.Choi WS.Kim KB.Woo TW.Lee SB.Chung YK. Can. J. Physiol. Pharmacol. 1999, 77: 330 - 13
Surgue MF.Gautheron P.Schmitt C.Viader MP.Conquet P.Smith RL.Share NN.Stone CA. J. Pharmacol. Exp. Ther. 1985, 232: 534 - 14
Phoon CW.Ng PY.Ting AE.Yeo SL.Sim MM. Bioorg. Med. Chem. Lett. 2001, 11: 1647 - 15
Loos D.Sidoova E.Sutoris V. Molecules 1999, 4: 81 ; and the references cited therein - 16
Ivanov SK.Yuritsyn VS. Neftekhimiya 1971, 11: 99 ; Chem. Abstr. 1971, 74, 124487m - 17 inventors; Monsanto Co., British Patent 1106577.
; Chem. Abstr. 1968, 68, 96660
- 18
Kashiyama E.Hutchinson I.Chua MS.Stinson SF.Phillips LR.Kaur G.Sausville EA.Bradshaw TD.Westwell AD.Stevens MFG. J. Med. Chem. 1999, 42: 4172 - 19
Boger DE. J. Org. Chem. 1978, 43: 2296 - 20
Cohen VI.Pourabass S. J. Heterocycl. Chem. 1977, 14: 1321 - 21
Cohen VI. J. Heterocycl. Chem. 1979, 16: 13 -
22a
Ben-Alloum A.Bakkas S.Soufiaoui M. Tetrahedron Lett. 1997, 38: 6395 -
22b
Bougrin K.Loupy A.Soufiaoui M. Tetrahedron 1998, 54: 8055 - 23
Abbotto A.Bradamante S.Facchetti A.Pagani GA. J. Org. Chem. 2002, 67: 5753 - 24
Matsushita H.Lee S.-H.Joung M.Clapham B.Janda KD. Tetrahedron Lett. 2004, 45: 313 -
25a
Roe A.Tucker WP. J. Heterocycl. Chem. 1965, 2: 148 -
25b
Yoshino K.Kohono T.Uno T.Moria T.Tsukamota G. J. Med. Chem. 1986, 29: 820 -
26a
Spitulnik M. Synthesis 1976, 730 -
26b
Hutchinson I.Stevens MFG.Westwell AD. Tetrahedron Lett. 2000, 41: 425 - 27
Rosini G.Medici A. Synthesis 1977, 892 - 28
Osuka A.Uno Y.Horiuchi H.Suzuki H. Synthesis 1984, 145 - 29
Perry RJ.Wilson BD. Organometallics 1994, 13: 3346 - 30
Paul S.Gupta M.Gupta R. Synth. Commun. 2002, 32: 3541 - 31
Majo VJ.Prabhakaran J.Mann JJ.Kumar JSD. Tetrahedron Lett. 2003, 44: 8535 - 32
Chakraborti AK.Selvam C.Kaur G.Bhagat S. Synlett 2004, 851 - 33
Chakraborti AK.Rudrawar S.Kaur G.Sharma L. Synlett 2004, 1533 - 34
Daltrozzo E, andReiss A. inventors; EP 1174430. ; Chem. Abstr. 2002, 136, p1184436 - 35
Brembilla A.Roizard D.Lochon P. Synth. Commun. 1990, 20: 3379 - 36
Mourtas S.Gatos D.Barlos K. Tetrahedron Lett. 2001, 42: 2201 -
37a
Chakraborti AK.Kaur G.Roy S. Indian J. Chem., Sect. B 2001, 40: 1000 -
37b
Chakraborti AK.Kaur G. Tetrahedron 1999, 55: 13265 - 38
Chakraborti AK.Sharma L.Nayak MK. J. Org. Chem. 2002, 67: 2541 - 39
Hosangadi BD.Dave RH. Tetrahedron Lett. 1996, 37: 6375 -
40a
Hilhorst E.Chen TBRA.Iskander AS.Pandit UK. Tetrahedron 1994, 50: 7837 -
40b
Ashby EC.Park W.-S.Goel AB.Su WY. J. Org. Chem. 1985, 50: 5184 -
40c
Surdhar PS.Armstrong DA. J. Phys. Chem. 1986, 90: 5915 ; and references therein -
40d
Evers M.Christiaens L. Tetrahedron Lett. 1983, 24: 377 - 41
Cogolli P.Maiolo F.Testaferri L.Tingoli M.Tiecco M. J. Org. Chem. 1979, 44: 2642 - 42
Cogolli P.Testaferri L.Tingoli M.Tiecco M. J. Org. Chem. 1979, 44: 2636 -
43a
Hwu JR.Wong FF.Shiao M.-J. J. Org. Chem. 1992, 57: 5254 -
43b
Shiao M.-J.Lai L.-L.Ku W.-S.Lin P.-Y.Hwu JR. J. Org. Chem. 1993, 58: 4742 -
44a
Chakraborti AK.Sharma L.Nayak MK. J. Org. Chem. 2002, 67: 6406 -
44b
Nayak MK.Chakraborti AK. Tetrahedron Lett. 1996, 38: 8749 -
44c
Chakraborti AK.Nayak MK.Sharma L. J. Org. Chem. 2002, 67: 1776 -
45a
Niyazymbetov ME.Laikhter AL.Semenov VV.Evans DH. Tetrahedron Lett. 1994, 35: 3037 -
45b
Tomioka K.Muraoka A.Kanai M. J. Org. Chem. 1995, 60: 6188 -
45c
Ito A.Konishi K.Aida T. Tetrahedron Lett. 1996, 37: 2585 -
46a
Katritzky I.Takahashi I.Marson CM. J. Org. Chem. 1986, 51: 4914 -
46b
Belley M.Zamboni R. J. Org. Chem. 1989, 54: 1230 - 47
Chen C.Chen YJ. Tetrahedron Lett. 2004, 45: 113