Sequential change in one-pot, three-component protocol: A stepping stone in heterocyclic synthesis

被引：14

作者：

Raja, Ranganathan ^{[1
]}

Murugan, Dinesh ^{[1
]}

Sivasubramaniyan, Archana ^{[1
]}

George, Jaabil ^{[1
]}

Perumal, Sakthivel ^{[1
]}

Alagusundaram, Ponnuswamy ^{[1
]}

Jayakumar, Mohan Raj ^{[2
]}

Saminathan, Murugavel ^{[2
]}

机构：

[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India

[2] Thanthai Periyar Govt Inst Technol, Dept Phys, Vellore, Tamil Nadu, India

来源：

SYNTHETIC COMMUNICATIONS | 2016年 / 46卷 / 11期

关键词：

Imidazole-2-thione; one pot; sequential change; stepping stone; thiazole-2-imine; three components; DERIVATIVES; IMIDAZOLE-2-THIONE; DESIGN;

D O I：

10.1080/00397911.2016.1178775

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two different heterocycles, thiazole-2-imines and imidazole-2-thiones, have been conveniently synthesized by just altering the sequential order (1 + 2 + 3 or 1 + 3 + 2) when combining the same components [aryl amine (1), aryl isothiocyanate (2), and phenacyl bromide (3)] in one-pot, three-component protocols. The third possible sequential order of combination (2 + 3 + 1) chemoselectively affords thiazole-2-imine. The finding is a stepping stone in the synthetic applicability of sequential one-pot, three-component protocols. [GRAPHICS] .

引用

页码：942 / 948

页数：7

共 26 条

[1] Synthesis and preliminary evaluation of some substituted coumarins as anticonvulsant agents [J].

Amin, Kamelia M. ;

Rahman, Doaa E. Abdel ;

Al-Eryani, Yasmin A. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (10) :5377-5388

[2] Powerful Approach to Heterocyclic Skeletal Diversity by Sequential Three-Component Reaction of Amines, Isothiocyanates, and 1,2-Diaza-1,3-dienes [J].

Attanasi, Orazio A. ;

Bartoccini, Silvia ;

Favi, Gianfranco ;

Giorgi, Gianluca ;

Perrulli, Francesca Romana ;

Santeusanio, Stefania .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) :1161-1167

[3] Aqueous-phase synthesis of 2-aminothiazole and 2-iminothiazolidine derivatives catalyzed by diammonium hydrogen phosphate and DABCO [J].

Balalaie, Saeed ;

Nikoo, Sahar ;

Haddadi, Shokat .

SYNTHETIC COMMUNICATIONS, 2008, 38 (15) :2521-2528

[4] Synthesis of new 2,5-diamino-1,3-thiazole and 2-thiohydantoin derivatives by condensation of N-(2-Aryl-1-chloro-2-oxoethyl) carboxamides with thioureas [J].

Balya, A. G. ;

Chernega, A. N. ;

But, S. A. ;

Vasilenko, A. N. ;

Brovarets, V. S. ;

Drach, B. S. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (07) :1427-1435

[5]

Bouchekara M., 2003, ARKIVOC, V10, P72

[6] Design, synthesis, and in vitro antitumor activity of new 1,4-diarylimidazole-2-ones and their 2-thione analogues [J].

Congiu, Cenzo ;

Cocco, Maria Teresa ;

Onnis, Valentina .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) :989-993

[7] Synthesis, reactions, and biological activity of 4,5-diarylimidazole-2-thiones (Review) [J].

Dawood, K. M. ;

Abdel-Wahab, B. F. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (03) :255-278

[8] An efficient synthesis of thiazol-2-imine derivatives via a one-pot, three-component reaction [J].

Heravi, Majid M. ;

Moghimi, Setareh .

TETRAHEDRON LETTERS, 2012, 53 (04) :392-394

[9]

Issa Y., 2014, J IRAN CHEM SOC, V11, P285

[10] Synthesis, characterization, and antibacterial activities of some novel N,N'-disubstituted thiourea, 2-amino thiazole, and imidazole-2-thione derivatives [J].

Kalhor, Mehdi ;

Salehifar, Mina ;

Nikokar, Iraj .

MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (06) :2947-2954

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