Novel Green Procedure for the Synthesis of 2-Arylbenzothiazoles Under Microwave Irradiation in Peg 200 Or Peg 400

被引:34
作者
Deligeorgiev, Todor G. [1 ]
Kaloyanova, Stefka [1 ]
Vasilev, Aleksey [1 ]
Vaquero, Juan J. [2 ]
机构
[1] Univ Sofia, Fac Chem, Sofia 1164, Bulgaria
[2] Univ Alcala, Fac Farm, Madrid, Spain
关键词
2-Aminothiophenols; arylbenzothiazoles; 2; 2'-diaminodiphenyldisulfides; green chemistry; microwave; SOLVENT-FREE SYNTHESIS; EFFICIENT SYNTHESIS; ANTITUMOR BENZOTHIAZOLES; CONDENSATION; DERIVATIVES; FACILE;
D O I
10.1080/10426501003598648
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An improved green procedure for the synthesis of 2-aryl- and 2-hetarylbenzothiazoles by condensation of equivalent amounts of 2,2'-diaminodiphenyldisulfides or 2-aminothiophenols and various aromatic aldehydes in PEG 200/400 under microwave irradiation has been developed. This method allows the synthesis of 2-arylbenzothiazoles in high yields and with high purity regardless of the state of the starting compounds (liquid or solid) or the nature of the substituents in the aromatic ring.
引用
收藏
页码:2292 / 2302
页数:11
相关论文
共 40 条
[1]   Synthesis of new fluorescent 2-(2′,2"-bithienyl)-1,3-benzothiazoles [J].
Batista, RMF ;
Costa, SPG ;
Raposo, MMM .
TETRAHEDRON LETTERS, 2004, 45 (13) :2825-2828
[2]   Novel synthesis of 2-arylbenzothiazoles - Microwave-activated electron transfer [J].
BenAlloum, A ;
Bakkas, S ;
Soufiaoui, M .
TETRAHEDRON LETTERS, 1997, 38 (36) :6395-6396
[3]  
Besson T, 2007, MICROWAVE ASSISTED ORGANIC SYNTHESIS, P44
[4]  
BOMBA C, 1994, 5371232 US
[5]   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
[6]   Fluorinated 2-(4-amino-3-methylphenyl) benzothiazoles induce CYP1A1 expression, become metabolized, and bind to macromolecules in sensitive human cancer cells [J].
Brantley, E ;
Trapani, V ;
Alley, MC ;
Hose, CD ;
Bradshaw, TD ;
Stevens, MFG ;
Sausville, EA ;
Stinson, SF .
DRUG METABOLISM AND DISPOSITION, 2004, 32 (12) :1392-1401
[7]   KUANONIAMINE-A, KUANONIAMINE-B, KUANONIAMINE-C, AND KUANONIAMINE-D - PENTACYCLIC ALKALOIDS FROM A TUNICATE AND ITS PROSOBRANCH MOLLUSK PREDATOR CHELYNOTUS-SEMPERI [J].
CARROLL, AR ;
SCHEUER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) :4426-4431
[8]   An efficient synthesis of benzothiazoles by direct condensation of carboxylic acids with 2-aminothiophenol under microwave irradiation [J].
Chakraborti, AK ;
Selvam, C ;
Kaur, G ;
Bhagat, S .
SYNLETT, 2004, (05) :851-855
[9]   A GENERAL AND EFFICIENT SYNTHESIS OF 2-PHENYLBENZOTHIAZOLES FROM DIPHENYL DISULFIDES [J].
CHANG, YH ;
PEAK, JD ;
WIERSCHKE, SW ;
FELD, WA .
SYNTHETIC COMMUNICATIONS, 1993, 23 (05) :663-670
[10]   Polyethylene glycol and solutions of polyethylene glycol as green reaction media [J].
Chen, J ;
Spear, SK ;
Huddleston, JG ;
Rogers, RD .
GREEN CHEMISTRY, 2005, 7 (02) :64-82