Methanesulfonic Acid/SiO2 as an Efficient Combination for the Synthesis of 2-Substituted Aromatic and Aliphatic Benzothiazoles from Carboxylic Acids

被引:82
作者
Sharghi, Hashem [1 ]
Asemani, Omid [2 ,3 ]
机构
[1] Shiraz Univ, Dept Chem, Shiraz 71454, Iran
[2] Shiraz Univ Med Sci, Fac Pharm, Dept Med Chem, Shiraz, Iran
[3] Shiraz Univ Med Sci, Res Ctr, Shiraz, Iran
关键词
2-Alkylbenzothiazoles; 2-arylbenzothiazoles; methanesulfonic acid; silica gel; ANTITUMOR BENZOTHIAZOLES; BIOLOGICAL-PROPERTIES; 2-ARYLBENZOTHIAZOLES; 2-(4-AMINOPHENYL)BENZOTHIAZOLES; BENZOXAZOLES; AMA; REARRANGEMENT; DERIVATIVES; REAGENT; AGENTS;
D O I
10.1080/00397910802431214
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methanesulfonic acid/SiO2 (1mL/0.3g) was found to be as an expeditious mixture in the synthesis of 2-substituted aromatic and aliphatic benzothiazoles at 140C using carboxylic acids. After a simple workup, benzothiazoles were obtained in good yields. Simplicity, use of widely available and diverse carboxylic acids, and easy handling of the reaction conditions are among the benefits of the method.
引用
收藏
页码:860 / 867
页数:8
相关论文
共 22 条
[1]  
Ali A., 2001, PCT Int Appl, Patent No. [W02001028561, 2001028561]
[2]  
Bergman J.M., 2006, PCT Int. Appl., Patent No. [WO 2006127550, 2006127550]
[3]   CONVENIENT PREPARATION OF 2-SUBSTITUTED BENZOTHIAZOLES [J].
BOGER, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11) :2296-2297
[4]   A convenient access to substituted benzothiazole scaffolds via intramolecular cyclization of thioformanilides [J].
Bose, D. Subhas ;
Idrees, Mohd. .
TETRAHEDRON LETTERS, 2007, 48 (04) :669-672
[5]   2-(4-aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity [J].
Bradshaw, TD ;
Wrigley, S ;
Shi, DF ;
Schultz, RJ ;
Paull, KD ;
Stevens, MFG .
BRITISH JOURNAL OF CANCER, 1998, 77 (05) :745-752
[6]   AN IMPROVED METHOD FOR THE PREPARATION OF 2-ARYL-BENZOTHIAZOLES, 2-HETARYL-BENZOTHIAZOLES AND 2-STYRYLBENZOTHIAZOLES [J].
DELIGEORGIEV, TG .
DYES AND PIGMENTS, 1990, 12 (04) :243-248
[7]   Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides [J].
Evindar, G ;
Batey, RA .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :1802-1808
[8]   THE USE OF POLYPHOSPHORIC ACID IN THE SYNTHESIS OF 2-ARYL-SUBSTITUTED AND 2-ALKYL-SUBSTITUTED BENZIMIDAZOLES, BENZOXAZOLES AND BENZOTHIAZOLES [J].
HEIN, DW ;
ALHEIM, RJ ;
LEAVITT, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (02) :427-429
[9]   Antitumor benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles [J].
Hutchinson, I ;
Chua, MS ;
Browne, HL ;
Trapani, V ;
Bradshaw, TD ;
Westwell, AD ;
Stevens, MFG .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (09) :1446-1455
[10]   The regiospecific synthesis of 5-and 7-monosubstituted and 5,6-disubstituted 2-arylbenzothiazoles [J].
Hutchinson, I ;
Stevens, MFG ;
Westwell, AD .
TETRAHEDRON LETTERS, 2000, 41 (03) :425-428