Synthesis of thiazolines by the reaction of aryl ketonitriles with cysteamine via microwave irradiation

被引:20
作者
Kamila, Sukanta [1 ]
Biehl, Edward R. [1 ]
机构
[1] So Methodist Univ, Dept Chem, Dallas, TX 75275 USA
关键词
D O I
10.1002/jhet.5570440220
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thiazolines were synthesized in a one-pot reaction in excellent yield using a newly developed methodology. Ketonitriles were directly condensed with cysteamine (2-amino-thioalcohol) via microwave irradiation at 210 degrees C for 10 minutes under solvent free conditions and without my solid support. All the compounds were characterized by H-1 nmr, C-13 nmr spectroscopy and elemental analyses.
引用
收藏
页码:407 / 409
页数:3
相关论文
共 28 条
[1]   THE SYNTHESIS OF OPTICALLY-ACTIVE THIAZOLINE AND THIAZOLE DERIVED PEPTIDES FROM N-PROTECTED ALPHA-AMINO-ACIDS [J].
BODEN, CDJ ;
PATTENDEN, G ;
YE, T .
SYNLETT, 1995, (05) :417-419
[2]   TOTAL SYNTHESIS OF THIANGAZOLE, A NOVEL INHIBITOR OF HIV-1 FROM POLYANGIUM SP [J].
BOYCE, RJ ;
MULQUEEN, GC ;
PATTENDEN, G .
TETRAHEDRON LETTERS, 1994, 35 (31) :5705-5708
[3]   A one step synthesis of thiazolines from esters [J].
Busacca, CA ;
Dong, Y ;
Spinelli, EM .
TETRAHEDRON LETTERS, 1996, 37 (17) :2935-2938
[4]   A rational approach to the design of selective substrates and potent nontransportable inhibitors of the excitatory amino acid transporter EAAC1 (EAAT3). New glutamate and aspartate analogues as potential neuroprotective agents [J].
Campiani, G ;
De Angelis, M ;
Armaroli, S ;
Fattorusso, C ;
Catalanotti, B ;
Ramunno, A ;
Nacci, V ;
Novellino, E ;
Grewer, C ;
Ionescu, D ;
Rauen, T ;
Griffiths, R ;
Sinclair, C ;
Fumagalli, E ;
Mennini, T .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (16) :2507-2510
[5]   Mild method for the synthesis of thiazolines from secondary and tertiary amides [J].
Charette, AB ;
Chua, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :908-909
[6]   Microwaves in organic synthesis.: Thermal and non-thermal microwave effects [J].
de la Hoz, A ;
Díaz-Ortiz, A ;
Moreno, A .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (02) :164-178
[7]   Benzamide bioisosteres incorporating dihydroheteroazole substructures:: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179) [J].
Einsiedel, J ;
Hübner, H ;
Gmeiner, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (18) :2533-2536
[8]   HETEROCYCLES FROM N-ETHOXYCARBONYLTHIOAMIDES AND DINUCLEOPHILIC REAGENTS .2. 5-MEMBERED RINGS CONTAINING 2 HETEROATOMS AT 1,3 POSITIONS [J].
GEORGE, B ;
PAPADOPOULOS, EP .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (03) :441-443
[9]   Facile syntheses of oxazolines and thiazolines with N-acylbenzotriazoles under microwave irradiation [J].
Katritzky, AR ;
Cai, CM ;
Suzuki, K ;
Singh, SK .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) :811-814
[10]   Thionation of N-(ω-halogenoalkyl)-substituted Amides with Lawesson's reagent:: Facile synthesis of 4,5-dihydro-t3-thiazoles and 5,6-dihydro-4H-1,3-thiazines [J].
Kodama, Y ;
Ori, M ;
Nishio, T .
HELVETICA CHIMICA ACTA, 2005, 88 (02) :187-193