o-lodoxybenzoic Acid Mediated Oxidative Desulfurization Initiated Domino Reactions for Synthesis of Azoles

被引:94
作者
Chaudhari, Pramod S. [1 ]
Pathare, Sagar P. [1 ]
Akamanchi, Krishnacharaya G. [1 ]
机构
[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, Maharashtra, India
关键词
IODOXYBENZOIC ACID; DERIVATIVES; INHIBITORS; IBX;
D O I
10.1021/jo2025509
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.
引用
收藏
页码:3716 / 3723
页数:8
相关论文
共 50 条
[1]   Multi-gram scale mercury-free synthesis of optically pure 3,4,5-trisubstituted 1,2,4-triazoles using silver benzoate [J].
Bibian, Mathieu ;
Blayo, Anne-Laure ;
Moulin, Aline ;
Martinez, Jean ;
Fehrentz, Jean-Alain .
TETRAHEDRON LETTERS, 2010, 51 (19) :2660-2663
[2]  
BRODA W, 1985, ISRAEL J CHEM, V26, P219
[3]   SUBSTITUTED 1,3,4-THIADIAZOLES WITH ANTICONVULSANT ACTIVITY .1. HYDRAZINES [J].
CHAPLEO, CB ;
MYERS, M ;
MYERS, PL ;
SAVILLE, JF ;
SMITH, ACB ;
STILLINGS, MR ;
TULLOCH, IF ;
WALTER, DS ;
WELBOURN, AP .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2273-2280
[4]   o-Iodoxybenzoic Acid Mediated Oxidative Desulfurization of 1,3-Disubstituted Thioureas to Carbodiimides [J].
Chaudhari, Pramod S. ;
Dangate, Prasad S. ;
Akamanchi, Krishnacharya G. .
SYNLETT, 2010, (20) :3065-3067
[5]   Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles [J].
Chekler, Eugene L. Piatnitski ;
Elokdah, Hassan M. ;
Butera, John .
TETRAHEDRON LETTERS, 2008, 49 (47) :6709-6711
[6]   MESOGENIC SEMICARBAZONES AND AMINO OXADIAZOLES-I [J].
CHUDGAR, NK ;
SHAH, SN ;
VORA, RA .
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1989, 172 :51-56
[7]  
De Clercq E, 2004, J CLIN VIROL, V30, P115, DOI [10.1016/j.jcv.2004.02.009, 10.1002/rmv.439]
[8]   Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles [J].
Dolman, Sarah J. ;
Gosselin, Francis ;
O'Shea, Paul D. ;
Davies, Ian W. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9548-9551
[9]   Synthesis and ring transformations of 1-amino-1,2,3,9a-tetrahydroimidazo[ 1,2-a]indol-2(9H)-ones [J].
Dumciute, J ;
Martynaitis, V ;
Holzer, W ;
Mangelinckx, S ;
De Kimpe, N ;
Sackus, A .
TETRAHEDRON, 2006, 62 (14) :3309-3319
[10]  
Ghirian D., 1974, FARMADA, V22, P141