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Synthesis 2007(4): 541-546
DOI: 10.1055/s-2007-965892
DOI: 10.1055/s-2007-965892
PAPER
© Georg Thieme Verlag Stuttgart · New York
Magnesium Perchlorate as a New and Highly Efficient Catalyst for the Synthesis of 2,3-Dihydro-1,5-benzothiazepines
Weitere Informationen
Received
11 September 2006
Publikationsdatum:
18. Januar 2007 (online)
Publikationsverlauf
Publikationsdatum:
18. Januar 2007 (online)
Abstract
Commercially available magnesium perchlorate has been found to be a highly efficient catalyst for the reaction of 1,3-diarylprop-2-enones with 2-aminothiophenol leading to the synthesis of 2,3-dihydro-1,5-benzothiazepines in high yields and in short times.
Key words
1,5-benzothiazepines - 2-aminothiophenol - 1,3-diarylprop-2-enones - magnesium perchlorate - catalyst - chemoselective
- 1
Sarro GD.Chimirri A.Sarro AD.Gitto R.Grasso S.Zappalá M. Eur. J. Med. Chem. 1995, 30: 925 -
2a
Shinichi Y.Yoshikazu M.Katsuji M.Yoshinori I.Yasuhiko O.Ryuzo Y.Tadashi N.Hiroyasu S. J. Org. Chem. 1996, 61: 8586 -
2b
Kurokawa J.Adachi-Akahane S.Nagao T. Eur. J. Pharmacol. 1997, 325: 229 - 3
Miyata O.Tetsuro S.Ichiya N.Takeaki N. Tetrahedron 1997, 53: 2421 - 4
Grandolini G.Perioli L.Ambrogi V. Eur. J. Med. Chem. 1999, 34: 701 - 5
Yang X.Buzon L.Hamanaka E.Liu KK.-C. Tetrahedron: Asymmetry 2000, 11: 4447 - 6
Urbanski MJ.Chen RH.Demarest KT.Gunnet J.Look R.Ericson E.Murray WV.Rybczynski PJ.Zhang X. Bioorg. Med. Chem. Lett. 2003, 13: 4031 - 7
Di Santo R.Costi R. Farmaco 2005, 60: 385 - 8
Lévai A. J. Heterocycl. Chem. 2000, 37: 199 - 9
Kodomari M.Noguchi T.Aoyama T. Synth. Commun. 2004, 34: 1783 - 10
Patel VM.Desai KR. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43: 199 -
11a
Lévai A. J. Heterocycl. Chem. 2004, 41: 399 -
11b
Lévai A. J. Heterocycl. Commun. 2002, 8: 227 -
11c
Lévai A. J. Heterocycl. Commun. 2002, 8: 375 - 12
Micheli F.Degiorgis F.Feriani A.Paio A.Pozzan A.Zarantonello P.Seneci P. J. Comb. Chem. 2001, 3: 224 - 13
Pant S.Singhal B.Upreti M.Pant U. Molecules 1998, 3: 159 -
14a
Upreti M.Pant S.Dandia A.Pant UC. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1997, 36: 1181 -
14b
Pant S.Sharma A.Sharma SK.Pant UC.Goel AK. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1996, 35: 794 - 15
Katritzky AR.Rogovoy BV.Chassaing C.Vvedensky V.Forood B.Flatt B.Nakai H. J. Heterocycl. Chem. 2000, 37: 1655 - 16
Dandia A.Sati M.Loupy A. Green Chem. 2002, 4: 599 - 17
Patel VM.Desai KR. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43: 199 - 18
Olah GA.Prakash GKS.Sommer J. Superacids Wiley; New York: 1985. -
19a
Steel PG. J. Chem. Soc., Perkin Trans. 1 2001, 2727 -
19b
Kobayashi S.Manabe K. Acc. Chem. Res. 2002, 35: 209 - 20
Dumeunier R.Markó IE. Tetrahedron Lett. 2004, 45: 825 - 21
Orita A.Tanahashi C.Kakuda A.Otera J. J. Org. Chem. 2001, 66: 8926 - 22
Qian C.Huang T. J. Org. Chem. 1998, 63: 4125 - 23
Foropoulos J.DesMarteau DD. Inorg. Chem. 1984, 23: 3720 - 24
Chakraborti AK.Shivani . J. Org. Chem. 2006, 71: 5785 ; and references cited therein - 25
Ishihara K.Kubota M.Yamamoto H. Synlett 1996, 265 - Thia-Michael addition:
-
26a
Garg SK.Kumar R.Chakraborti AK. Tetrahedron Lett. 2005, 46: 1721 -
26b
Garg SK.Kumar R.Chakraborti AK. Synlett 2005, 1370 - Acylation:
-
26c
Chakraborti AK.Sharma L.Gulhane R.Shivani . Tetrahedron 2003, 59: 7661 -
26d
Chakraborti AK.Gulhane R.Shivani . Synlett 2003, 1805 - Imine formation:
-
26e
Chakraborti AK.Bhagat S.Rudrawar S. Tetrahedron Lett. 2004, 45: 7641 - Acylal formation:
-
26f
Kumar R.Thilagavathi R.Gulhane R.Chakraborti AK. J. Mol. Catal. A: Chem. 2006, 250: 227 - 27
Cogolli P.Maiolo F.Testaferri L.Tingoli M.Tiecco M. J. Org. Chem. 1979, 44: 2642 - 28
Cogolli P.Testaferri L.Tingoli M.Tiecco M. J. Org. Chem. 1979, 44: 2636 -
29a
Hwu JR.Wong FF.Shiao M.-J. J. Org. Chem. 1992, 57: 5254 -
29b
Shiao M.-J.Lai L.-L.Ku W.-S.Lin P.-Y.Hwu JR. J. Org. Chem. 1993, 58: 4742 -
30a
Katritzky I.Takahashi I.Marson CM. J. Org. Chem. 1986, 51: 4914 -
30b
Belley M.Zamboni R. J. Org. Chem. 1989, 54: 1230 -
31a
Hilhorst E.Chen TBRA.Iskander AS.Pandit UK. Tetrahedron 1994, 50: 7837 -
31b
Surdhar PS.Armstrong DA. J. Phys. Chem. 1986, 90: 5915 -
31c
Ashby EC.Park W.-S.Goel AB.Su WY. J. Org. Chem. 1985, 50: 5184 -
32a
Gavande NS.Kundu S.Badgujar NS.Kaur G.Chakraborti AK. Tetrahedron 2006, 62: 4201 -
32b
Chakraborti AK.Sharma L.Nayak MK. J. Org. Chem. 2002, 67: 6406 -
32c
Chakraborti AK.Sharma L.Nayak MK. J. Org. Chem. 2002, 67: 2541 -
32d
Chakraborti AK.Nayak MK.Sharma L. J. Org. Chem. 2002, 67: 1776 -
32e
Nayak MK.Chakraborti AK. Tetrahedron Lett. 1997, 38: 8749 - 33
Chakraborti AK.Nayak MK.Sharma L. J. Org. Chem. 1999, 64: 8027 -
34a
Sharma L.Nayak MK.Chakraborti AK. Tetrahedron 1999, 55: 9595 -
34b
Nayak MK.Chakraborti AK. Chem. Lett. 1998, 297