An Efficient Synthesis of Benzothiazoles by Direct Condensation of Carboxylic Acids with 2-Aminothiophenol under Microwave Irradiation

Asit K. Chakraborti; C. Selvam; Gurmeet Kaur; Srikant Bhagat

doi:10.1055/s-2004-820012

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2004(5): 0851-0855
DOI: 10.1055/s-2004-820012

LETTER

An Efficient Synthesis of Benzothiazoles by Direct Condensation of Carboxylic Acids with 2-Aminothiophenol under Microwave Irradiation

Asit K. Chakraborti*, C. Selvam, Gurmeet Kaur, Srikant Bhagat
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;

Further Information

Publication History

Received 14 November 2003
Publication Date:
24 February 2004 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Carboxylic acids are converted to benzothiazoles by direct condensation with 2-aminothiophenol under microwave irradiation in the absence of solvent.

Key words

benzothiazoles - carboxylic acids - 2-aminothiophenol - solvent-free - microwave

References

1a Hall IH. Peaty NJ. Henry JR. Easmon J. Heinisch G. Purstinger G. Arch. Pharm. 1999, 332: 115

Crossref Google Scholar
1b Bénéteau V. Besson T. Guillard J. Léonce S. Pfeiffer B. Eur. J. Med. Chem. 1999, 34: 1053

Crossref Google Scholar
1c Hutchinson I. Bradshaw TD. Matthews-Stevens MFG. Westwell AD. Bioorg. Med. Chem. Lett. 2003, 13: 471 ; and the references therein

Crossref Google Scholar
2 Palmer PJ. Trigg RB. Warrington JV. J. Med. Chem. 1971, 14: 248

Crossref Google Scholar
3a Benazzouz A. Boraud T. Dubédat P. Boireau A. Stutzmann J.-M. Gross C. Eur. J. Pharmacol. 1995, 284: 299

Crossref PubMed Google Scholar
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

Crossref PubMed Google Scholar
4 Lara B. Gandia L. Tores A. Martinez-Sierra R. Garcia AG. Lopez MG. Eur. J. Pharmacol. 1997, 325: 109

Crossref Google Scholar
5a Mylari BL. Larson ER. Beyer TA. Zembrowski WJ. Aldinger CE. Dee MF. Siegel TW. Singleton DH. J. Med. Chem. 1991, 34: 108

Crossref Google Scholar
5b Kotani T. Nagaki Y. Ishii A. Konishi Y. Yago H. Suehiro S. Okukado N. Okamoto K. J. Med. Chem. 1997, 40: 684

Crossref Google Scholar
6a Sato G. Chimoto T. Aoki T. Hosokawa S. Sumigama S. Tsukidate K. Sagami F. J. Toxicol. Sci. 1999, 24: 165

Google Scholar
6b Naitoh T. Kawaguchi S. Kakiki M. Ohe H. Kajiwara A. Horie T. Xenobiotica 1998, 28: 269

Google Scholar
6c Kagaya T. Kajiwara A. Nagato S. Akasaka K. Kubota A. J. Pharmacol. Exp. Ther. 1996, 278: 243

Google Scholar
7a Hadjipavlou-Litina DJ. Geronikaki AA. Drug Des. Discovery 1997, 15: 199

Crossref Google Scholar
7b Oketani K. Inoue T. Murakami M. Eur. J. Pharmacol. 2001, 427: 159

Crossref Google Scholar
8 Paramashivappa R. Phani Kumar P. Subba Rao PV. Srinivasa Rao A. Bioorg. Med. Chem. Lett. 2003, 13: 657

Crossref Google Scholar
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

Crossref Google Scholar
10 Matthews JH. Krishnan R. Costanzo MJ. Maryanoff BE. Tulinsky A. Biophys. J. 1996, 2830

Google Scholar
11 Caccese RG. DiJoseph JF. Scotnicki JS. Borella LE. Adams LM. Agents Actions 1991, 34: 223

Crossref Google Scholar
12 Sohn SK. Chang MS. Choi WS. Kim KB. Woo TW. Lee SB. Chung YK. Can. J. Physiol. Pharmacol. 1999, 77: 330

Crossref Google Scholar
13 Surgue MF. Gautheron P. Schmitt C. Viader MP. Conquet P. Smith RL. Share NN. Stone CA. J. Pharmacol. Exp. Ther. 1985, 232: 534

Google Scholar
14 Phoon CW. Ng PY. Ting AE. Yeo SL. Sim MM. Bioorg. Med. Chem. Lett. 2001, 11: 1647

Crossref Google Scholar
15 Loos D. Sidoova E. Sutoris V. Molecules 1999, 4: 81 ; and the references cited therein

Crossref Google Scholar
16 Ivanov SK. Yuritsyn VS. Neftekhimiya 1971, 11: 99 ; Chem. Abstr. 1971, 74, 124487m

Google Scholar
17 inventors; Monsanto Co. Brit. Pat. 1,106,577. ; Chem. Abstr. 1968, 68, 96660t
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

Crossref Google Scholar
19 Boger DE. J. Org. Chem. 1978, 43: 2296

Crossref Google Scholar
20 Cohen VI. Pourabass S. J. Heterocycl. Chem. 1977, 14: 1321

Crossref Google Scholar
21 Cohen VI. J. Heterocycl. Chem. 1979, 16: 13

Crossref Google Scholar
22 Ben-Alloum A. Bakkas S. Soufiaoui M. Tetrahedron Lett. 1997, 38: 6395

Crossref Google Scholar
23a Roe A. Tucker WP. J. Heterocycl. Chem. 1965, 148

Crossref Google Scholar
23b Yoshino K. Kohono T. Uno T. Moria T. Tsukamota G. J. Med. Chem. 1986, 29: 820

Crossref Google Scholar
24a Spitulnik M. Synthesis 1976, 730

Crossref Google Scholar
24b Hutchinson I. Stevens MFG. Westwell AD. Tetrahedron Lett. 2000, 41: 425

Crossref Google Scholar
25 Rosini G. Medici A. Synthesis 1977, 892

Article in Thieme Connect Google Scholar
26 Osuka A. Uno Y. Horiuchi H. Suzuki H. Synthesis 1984, 145

Article in Thieme Connect Google Scholar
27 Perry RJ. Wilson BD. Organometallics 1994, 13: 3346

Crossref Google Scholar
28 Paul S. Gupta M. Gupta R. Synth. Commun. 2002, 32: 3541

Crossref Google Scholar
29a Evers M. Christiaens L. Tetrahedron Lett. 1983, 24: 377

Crossref Google Scholar
29b Ashby EC. Park W.-S. Goel AB. Su WY.
J. Org. Chem. 1985, 50: 5184

Crossref Google Scholar
29c Surdhar PS. Armstrong DA. J. Phys. Chem. 1986, 90: 5915 ; and references therein

Crossref Google Scholar
29d Hilhorst E. Chen TBRA. Iskander AS. Pandit UK. Tetrahedron 1994, 50: 7837

Crossref Google Scholar
30 Cogolli P. Maiolo F. Testaferri L. Tingoli M. Tiecco M. J. Org. Chem. 1979, 44: 2642

Crossref Google Scholar
31a Chakraborti AK. Sharma L. Nayak MK. J. Org. Chem. 2002, 67: 6404

Google Scholar
31b Chakraborti AK. Nayak MK. Sharma L. J. Org. Chem. 2002, 67: 2541

Google Scholar
31c Chakraborti AK. Nayak MK. Tetrahedron Lett. 1996, 38: 8749

Google Scholar
32a Lawrance WW. Tetrahedron Lett. 1971, 3543

Article in Thieme Connect Google Scholar
32b Terashima M. Ishii M. Kanaoka Y. Synthesis 1982, 484

Article in Thieme Connect Google Scholar
33a Niyazymbetov ME. Laikhter AL. Semenov VV. Evans DH. Tetrahedron Lett. 1994, 35: 3037

Crossref Google Scholar
33b Tomioka K. Muraoka A. Kanai M. J. Org. Chem. 1995, 60: 6188

Crossref Google Scholar
33c Ito A. Konishi K. Aida T. Tetrahedron Lett. 1996, 37: 2585

Crossref Google Scholar
34a Katrizky I. Takahashi I. Marson CM. J. Org. Chem. 1986, 51: 4914

Crossref Google Scholar
34b Belley M. Zamboni R. J. Org. Chem. 1989, 54: 1230

Crossref Google Scholar
35 Metzer J. Plank H. Bull. Soc. Chim. Fr. 1956, 1652

Google Scholar
36 Charrier J.-D. Landreau C. Deniaud D. Reliquet F. Reliquet A. Meslin JC. Tetrahedron 2001, 57: 4195

Crossref Google Scholar
37 Courtot C. Tchelitcheff S. Compt. Rend. 1943, 217: 231

Google Scholar
38a Isikdag I. Ucucu U. Doga: Turk Saglik Bilimleri Dergisi 1990, 14: 158

Google Scholar
38b Mettery Y. Michaud S. Vierfond JM. Heterocycles 1994, 38: 1001

Google Scholar
39 Prescott B. Webb JM. Antibiotics and Chemotherapy 1958, 8: 33

Google Scholar
40 Cuadro A. Perez-Butragueno J. Pastor-Masco M. Alvarez-Builla J. Martincz-Grueiro MM. Martinez-Fernandez AR. Farmaco 1992, 47: 477 ; Chem. Abstr. 1992, 117, 225777t

Google Scholar
41 Towle JL. Iowa State Coll. J. Sci. 1952, 26: 308 ; Chem. Abstr. 1953, 47, 8063b

Google Scholar
42 Majo VJ. Prabhakaran J. Mann JJ. Kumar JSD. Tetrahedron Lett. 2003, 44: 8535

Crossref Google Scholar
43 Baum JS, and Chen Tsong M. inventors; U.S. Patent No. 4556411.