Solid-phase syntheses of 1,2,4-trisubstituted urazole and thiourazole derivatives

被引：10

作者：

Phoon, CW ^{[1
]}

Sim, MM ^{[1
]}

机构：

[1] Inst Mol & Cell Biol, Med & Combinatorial Chem Lab, Singapore 117609, Singapore

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2002年 / 4卷 / 05期

关键词：

D O I：

10.1021/cc0200134

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Solid-phase syntheses of 1,2,4-trisubstituted urazole and thiourazole derivatives have been accomplished. The synthesis began with the coupling of carbonylimidazole-Wang resin with a disubstituted hydrazine. The resultant carbazate was coupled with an isocyanate or isothiocyanate. Subsequent heating of the resin in the presence of triethylamine or potassium t-butoxide induced cyclization and released the desired (thio)urazole into solution. Most of the products were obtained in high yields and purities. Structural diversity can be further expanded at the R-2 substituent by performing the palladium-mediated Suzuki coupling reaction.

引用

页码：491 / 495

页数：5

共 50 条

[21] A facile and efficient method for the synthesis of 1,2,4-trisubstituted imidazoles with enamides and benzylamines
Cao, Jinhui
Zhou, Xiaoqiang
Ma, Haojie
Shi, Chong
Huang, Guosheng
RSC ADVANCES, 2016, 6 (62) : S7232 - S7235
[22] Investigation of the biological roles of 1,4-disubstituted and 1,2,4-trisubstituted cyclohexadienes
Bench, Bennie J.
Liu, Chaomin
Watanabe, Coran M. H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[23] Regioselective synthesis of 1,2,4-trisubstituted imidazole from a mechanistic and synthetic prospective
Punia, Suman
Verma, Vikas
Kumar, Devinder
Singh, Gurjaspreet
Sahoo, Subash C.
SYNTHETIC COMMUNICATIONS, 2020, 50 (05) : 700 - 709
[24] DIPOLE-MOMENTS AND QUESTIONS CONCERNING STRUCTURE OF 1,2,4-TRISUBSTITUTED BENZENE AND 1,2,5-TRISUBSTITUTED BENZENE
LUTSKII, AE
KOLESNIK, MI
OBUKHOVA, EM
ZHURNAL OBSHCHEI KHIMII, 1972, 42 (06): : 1394 - &
[25] Solid-phase synthesis of trisubstituted guanidines
Drewry, DH
Gerritz, SW
Linn, JA
TETRAHEDRON LETTERS, 1997, 38 (19) : 3377 - 3380
[26] Extending the scope of a known furan synthesis -: A novel route to 1,2,4-trisubstituted pyrroles
Friedrich, M
Wächtler, A
de Meijere, A
SYNLETT, 2002, (04) : 619 - 621
[27] MASS-SPECTRA OF 1,2,4-TRISUBSTITUTED 5-FUNCTIONALIZED 2-IMIDAZOLINES
BOSSO, C
MARSURA, A
LUUDUC, C
ORGANIC MASS SPECTROMETRY, 1985, 20 (03): : 263 - 264
[28] Synthesis and investigation of the biological roles of 1,4-disubstituted and 1,2,4-trisubstituted cyclohexadienes
Benson, Jenna M.
Bench, Bennie J.
Watanabe, Coran M. H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 104 - 104
[29] Expeditious synthesis of novel NK1 antagonists based on a 1,2,4-trisubstituted cyclohexane
Dirat, O
Elliott, JM
Jelley, RA
Jones, AB
Reader, M
TETRAHEDRON LETTERS, 2006, 47 (08) : 1295 - 1298
[30] APPLICATION OF LIGAND ASSISTED NUCLEOPHILIC ADDITIONS - SYNTHESIS OF 1,2,4-TRISUBSTITUTED AROMATIC SYSTEMS
MARYANOFF, CA
CHERRY, DA
MILLS, JE
PARAGAMIAN, V
LIOTTA, D
JAMISON, WCL
SOLOMON, M
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 194 : 120 - ORGN

← 1 2 3 4 5 →