Eco-Friendly Synthesis of Some Thiosemicarbazones and Their Applications as Intermediates for 5-Arylazothiazole Disperse Dyes

被引：17

作者：

Gaffer, Hatem E. ^{[1
]}

Khalifa, Mohamed E. ^{[2
,3
]}

机构：

[1] Natl Res Ctr, Text Res Div, Dokki 12622, Egypt

[2] Taif Univ, Dept Chem, Fac Sci, At Taif 21974, Saudi Arabia

[3] Higher Inst Engn & Technol, Dept Chem Engn, Cent Zone, Dumyat, Egypt

来源：

MOLECULES | 2015年 / 20卷 / 12期

关键词：

solid-solid reactions; thiosemicarbazones; phenacyl bromide; 5-arylazothiazoles; disperse dyes; fastness properties; RIBONUCLEOTIDE REDUCTASE; DERIVATIVES; COMPLEXES; IRON(III); BEHAVIOR;

D O I：

10.3390/molecules201219820

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The solid-solid reactions of thiosemicarbazide with 4-formylantipyrine, 2-acetylpyrrole and camphor were performed to afford the thiosemicarbazones 1-3 which underwent hetero-cyclization with phenacyl bromide to furnish the corresponding thiazole derivatives 4-6. The yields of the reactions are quantitative in all cases and the products do not require further purification. A series of 5-arylazo-2-(substituted ylidene-hydrazinyl)-thiazole dyes 7-9 was then prepared by diazo coupling of thiazole derivatives 4-6 with several diazonium chlorides. The synthesized dyes were applied as disperse dyes for dyeing polyester fabric. The dyed fabrics exhibit good washing, perspiration, sublimation and light fastness properties, with little variation in their moderate to good rubbing fastness.

引用

页码：21982 / 21991

页数：10

共 23 条

[1] Abdel-Latif E, 2005, J CHEM RES, P187
[2] Waste-free solid-state organic syntheses: Solvent-free alkylation, heterocyclization, and azo-coupling reactions
Abdel-Latif, Ehab
Metwally, Mohamed A.
[J]. MONATSHEFTE FUR CHEMIE, 2007, 138 (08): : 771 - 776
[3] A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior
Al-Etaibi, Alya M.
El-Apasery, Morsy A.
Ibrahim, Maher R.
Al-Awadi, Nouria A.
[J]. MOLECULES, 2012, 17 (12) : 13891 - 13909
[4] The supramolecular chemistry of thiosemicarbazones derived from pyrrole:: a structural view
Alonso, R
Bermejo, E
Carballo, R
Castiñeiras, A
Pérez, T
[J]. JOURNAL OF MOLECULAR STRUCTURE, 2002, 606 (1-3) : 155 - 173
[5] Study of electronic and structural features of thiosemicarbazone and thiosemicarbazide derivatives demonstrating anti-HSV-1 activity
Altun, A
Kumru, M
Dimoglo, A
[J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2001, 535 : 235 - 246
[6] The wide pharmacological versatility of semicarbazones, thiosemicarbazones and their metal complexes
Beraldo, H
Gambino, D
[J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2004, 4 (01) : 31 - 39
[7] Eco-friendly solvent-free synthesis of thiazolylpyrazole derivatives
Bondock, Samir
El-Azap, Hossam
Kandeel, Ez-Eldin M.
Metwally, Mohamed A.
[J]. MONATSHEFTE FUR CHEMIE, 2008, 139 (11): : 1329 - 1335
[8] Equilibrium and kinetic studies of iron(II) and iron(III) complexes of some alpha(N)-heterocyclic thiosemicarbazones. Reduction of the iron(III) complexes of 2-formylpyridine thiosemicarbazone and 2-acetylpyridine thiosemicarbazone by cellular thiol-like reducing agents
Borges, RHU
Paniago, E
Beraldo, H
[J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 1997, 65 (04) : 267 - 275
[9] Behavior of thiosemicarbazones derived from some terpenones under acetylating conditions
Brousse, BN
Moglioni, AG
Alho, MM
Alvarez-Larena, A
Moltrasio, GY
D'Accorso, NB
[J]. ARKIVOC, 2002, : 14 - 23
[10] CHIPALKATTI HR, 1954, J SOC DYERS COLOUR, V70, P487

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