Magnesium Perchlorate as a New and Highly Efficient Catalyst for the Synthesis of 2,3-Dihydro-1,5-benzothiazepines

Gopal L. Khatik; Raj Kumar; Asit K. Chakraborti

doi:10.1055/s-2007-965892

PAPER

Magnesium Perchlorate as a New and Highly Efficient Catalyst for the Synthesis of 2,3-Dihydro-1,5-benzothiazepines

Gopal L. Khatik, Raj Kumar, Asit K. Chakraborti*
National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160062, India
Fax: +91(172)2214692; e-Mail: akchakraborti@niper.ac.in;

Abstract

All articles of this category

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

Full Text

References

<A NAME="RZ18706SS-1">1</A> Sarro GD. Chimirri A. Sarro AD. Gitto R. Grasso S. Zappalá M. Eur. J. Med. Chem. 1995, 30: 925

<A NAME="RZ18706SS-2A">2a</A> Shinichi Y. Yoshikazu M. Katsuji M. Yoshinori I. Yasuhiko O. Ryuzo Y. Tadashi N. Hiroyasu S. J. Org. Chem. 1996, 61: 8586

<A NAME="RZ18706SS-2B">2b</A> Kurokawa J. Adachi-Akahane S. Nagao T. Eur. J. Pharmacol. 1997, 325: 229

<A NAME="RZ18706SS-3">3</A> Miyata O. Tetsuro S. Ichiya N. Takeaki N. Tetrahedron 1997, 53: 2421

<A NAME="RZ18706SS-4">4</A> Grandolini G. Perioli L. Ambrogi V. Eur. J. Med. Chem. 1999, 34: 701

<A NAME="RZ18706SS-5">5</A> Yang X. Buzon L. Hamanaka E. Liu KK.-C. Tetrahedron: Asymmetry 2000, 11: 4447

<A NAME="RZ18706SS-6">6</A> 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

<A NAME="RZ18706SS-7">7</A> Di Santo R. Costi R. Farmaco 2005, 60: 385

<A NAME="RZ18706SS-8">8</A> Lévai A. J. Heterocycl. Chem. 2000, 37: 199

<A NAME="RZ18706SS-9">9</A> Kodomari M. Noguchi T. Aoyama T. Synth. Commun. 2004, 34: 1783

<A NAME="RZ18706SS-10">10</A> Patel VM. Desai KR. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43: 199

<A NAME="RZ18706SS-11A">11a</A> Lévai A. J. Heterocycl. Chem. 2004, 41: 399

<A NAME="RZ18706SS-11B">11b</A> Lévai A. J. Heterocycl. Commun. 2002, 8: 227

<A NAME="RZ18706SS-11C">11c</A> Lévai A. J. Heterocycl. Commun. 2002, 8: 375

<A NAME="RZ18706SS-12">12</A> Micheli F. Degiorgis F. Feriani A. Paio A. Pozzan A. Zarantonello P. Seneci P. J. Comb. Chem. 2001, 3: 224

<A NAME="RZ18706SS-13">13</A> Pant S. Singhal B. Upreti M. Pant U. Molecules 1998, 3: 159

<A NAME="RZ18706SS-14A">14a</A> Upreti M. Pant S. Dandia A. Pant UC. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1997, 36: 1181

<A NAME="RZ18706SS-14B">14b</A> Pant S. Sharma A. Sharma SK. Pant UC. Goel AK. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1996, 35: 794

<A NAME="RZ18706SS-15">15</A> Katritzky AR. Rogovoy BV. Chassaing C. Vvedensky V. Forood B. Flatt B. Nakai H. J. Heterocycl. Chem. 2000, 37: 1655

<A NAME="RZ18706SS-16">16</A> Dandia A. Sati M. Loupy A. Green Chem. 2002, 4: 599

<A NAME="RZ18706SS-17">17</A> Patel VM. Desai KR. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43: 199

<A NAME="RZ18706SS-18">18</A> Olah GA. Prakash GKS. Sommer J. Superacids Wiley; New York: 1985.

<A NAME="RZ18706SS-19A">19a</A> Steel PG. J. Chem. Soc., Perkin Trans. 1 2001, 2727

<A NAME="RZ18706SS-19B">19b</A> Kobayashi S. Manabe K. Acc. Chem. Res. 2002, 35: 209

<A NAME="RZ18706SS-20">20</A> Dumeunier R. Markó IE. Tetrahedron Lett. 2004, 45: 825

<A NAME="RZ18706SS-21">21</A> Orita A. Tanahashi C. Kakuda A. Otera J. J. Org. Chem. 2001, 66: 8926

<A NAME="RZ18706SS-22">22</A> Qian C. Huang T. J. Org. Chem. 1998, 63: 4125

<A NAME="RZ18706SS-23">23</A> Foropoulos J. DesMarteau DD. Inorg. Chem. 1984, 23: 3720

<A NAME="RZ18706SS-24">24</A> Chakraborti AK. Shivani . J. Org. Chem. 2006, 71: 5785 ; and references cited therein

<A NAME="RZ18706SS-25">25</A> Ishihara K. Kubota M. Yamamoto H. Synlett 1996, 265

Thia-Michael addition:

<A NAME="RZ18706SS-26A">26a</A> Garg SK. Kumar R. Chakraborti AK. Tetrahedron Lett. 2005, 46: 1721

<A NAME="RZ18706SS-26B">26b</A> Garg SK. Kumar R. Chakraborti AK. Synlett 2005, 1370

Acylation:

<A NAME="RZ18706SS-26C">26c</A> Chakraborti AK. Sharma L. Gulhane R. Shivani . Tetrahedron 2003, 59: 7661

<A NAME="RZ18706SS-26D">26d</A> Chakraborti AK. Gulhane R. Shivani . Synlett 2003, 1805

Imine formation:

<A NAME="RZ18706SS-26E">26e</A> Chakraborti AK. Bhagat S. Rudrawar S. Tetrahedron Lett. 2004, 45: 7641

Acylal formation:

<A NAME="RZ18706SS-26F">26f</A> Kumar R. Thilagavathi R. Gulhane R. Chakraborti AK. J. Mol. Catal. A: Chem. 2006, 250: 227

<A NAME="RZ18706SS-27">27</A> Cogolli P. Maiolo F. Testaferri L. Tingoli M. Tiecco M. J. Org. Chem. 1979, 44: 2642

<A NAME="RZ18706SS-28">28</A> Cogolli P. Testaferri L. Tingoli M. Tiecco M. J. Org. Chem. 1979, 44: 2636

<A NAME="RZ18706SS-29A">29a</A> Hwu JR. Wong FF. Shiao M.-J. J. Org. Chem. 1992, 57: 5254

<A NAME="RZ18706SS-29B">29b</A> Shiao M.-J. Lai L.-L. Ku W.-S. Lin P.-Y. Hwu JR. J. Org. Chem. 1993, 58: 4742

<A NAME="RZ18706SS-30A">30a</A> Katritzky I. Takahashi I. Marson CM. J. Org. Chem. 1986, 51: 4914

<A NAME="RZ18706SS-30B">30b</A> Belley M. Zamboni R. J. Org. Chem. 1989, 54: 1230

<A NAME="RZ18706SS-31A">31a</A> Hilhorst E. Chen TBRA. Iskander AS. Pandit UK. Tetrahedron 1994, 50: 7837

<A NAME="RZ18706SS-31B">31b</A> Surdhar PS. Armstrong DA. J. Phys. Chem. 1986, 90: 5915

<A NAME="RZ18706SS-31C">31c</A> Ashby EC. Park W.-S. Goel AB. Su WY. J. Org. Chem. 1985, 50: 5184

<A NAME="RZ18706SS-32A">32a</A> Gavande NS. Kundu S. Badgujar NS. Kaur G. Chakraborti AK. Tetrahedron 2006, 62: 4201

<A NAME="RZ18706SS-32B">32b</A> Chakraborti AK. Sharma L. Nayak MK. J. Org. Chem. 2002, 67: 6406

<A NAME="RZ18706SS-32C">32c</A> Chakraborti AK. Sharma L. Nayak MK. J. Org. Chem. 2002, 67: 2541

<A NAME="RZ18706SS-32D">32d</A> Chakraborti AK. Nayak MK. Sharma L. J. Org. Chem. 2002, 67: 1776

<A NAME="RZ18706SS-32E">32e</A> Nayak MK. Chakraborti AK. Tetrahedron Lett. 1997, 38: 8749

<A NAME="RZ18706SS-33">33</A> Chakraborti AK. Nayak MK. Sharma L. J. Org. Chem. 1999, 64: 8027

<A NAME="RZ18706SS-34A">34a</A> Sharma L. Nayak MK. Chakraborti AK. Tetrahedron 1999, 55: 9595

<A NAME="RZ18706SS-34B">34b</A> Nayak MK. Chakraborti AK. Chem. Lett. 1998, 297