Generally, the condensation of ophenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis. This compound which is bicyclic consists of the fusion of benzene 1 and imidazole 2 also known as benzimidazole 3 scheme 1. The synthesis and chemistry of certain anthelmintic benzimidazoles lb. Imidazole and benzimidazole synthesis is a comprehensive survey of. Journal of chemistry and biochemistry december 2014, vol. Molecules having benzimidazole motifs showed promising application in biological and clinical studies. Imidazole and benzimidazole synthesis sciencedirect. Similar results were obtained for imidazole with itf 182, a novel drug called selezen that consists of the salt of protonated imidazole and 2hydroxybenzoate in 1. Baran, richter essentials of heterocyclic chemistryi. Purchase imidazole and benzimidazole synthesis 1st edition. Only compounds 55 and 58 showed medium cytotoxic activities, and compound 59 with a naphthylacyl substituent at position3 of the imidazole ring. Imidazole is an entity which has interesting physical and chemical properties, in the present article focus lies on analysis of these properties which in turn may be exploited for different pharmacological activities, like compounds having a 3,4,5trimethoxyphenyl ring linked to either n1 or c4 position of the imidazole entity gave an. The newly synthesized compounds were characterized by 1 h and 31 p nmr, and maldi ms spectrometry.
Imidazole and its derivatives and importance in the synthesis of pharmaceuticals. The chemistry and biological significance of imidazole. This book chapter mainly discussed recent synthetic methods. The synthesis and chemistry of certain anthelmintic. Benzimidazole is formed by the fusion of benzene and imidazole moiety, and. Imidazole and benzimidazole modified halfsandwich iridiumiii nheterocyclic carbene complexes. Wise a basis for interest in the benzimidazole ring system as a nucleus from which to develop potential chemotherapeutic agents was established in the i95os when it was found that 5,6dimethyl i. Imidazole and benzimidazole synthesis ebook, 1997 worldcat. Imidazole and its derivatives and importance in the synthesis. Introduction imidazole 1, 3diaza2,4cyclopentadiene is a planner fivemember ring system with 3c and 2n atom in 1 and 3 positions. Development of drugs based on imidazole and benzimidazole. This reaction will give substantial yields only if the 1vinyltetrazole is made efficiently from an organotin compound, such as 2tributylstannyltetrazole. It brings together the multitude of syntheses of the imidazole ring in a systematic way in terms of specific bond formation. Imidazoles and benzimidazoles are molecules of wide interest and importance, especially with regard to their pharmaceutical applications.
Imidazole and its derivatives and importance in the. The synthesized materials include not only small coordination complexes but also isolated crystals. Combination of an alkene, carbon monoxide and ammonia r 2. Imidazole reached peak plasma levels within 15 to 30 minutes in rats dosed with approximately 17 mgkg bw and disappeared within 4 hours. Imidazole is a fivemembered heterocyclic compound with formula c 3 h 4 n 2. This book is not a procedural manual, it contains many useful preps.
The configurations of geometric isomers were analyzed by xray crystallography and 31 p nmr. M r grimmett imidazoles and benzimidazoles are molecules of wide interest and importance, especially with regard to their pharmaceutical applications. Actually, all classical syntheses of benzimidazoles represent modifications to two of the classic reactions. This bicyclic compound consists of the fusion of benzene and imidazole. Benzimidazole is a heterocyclic aromatic organic compound. Similar books to imidazole and benzimidazole synthesis issn. Imidazoles and benzimidazoles are molecules of wide. The imidazole, benzimidazole, benzoxazole, tetrazole and quinazolinone are.
Synthesis and antibacterial evaluation of some novel imidazole and benzimidazole sulfonamides by nassir n. Imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. Benzimidazole and its derivatives are regarded as an important heterocyclic motif that exhibits a wide range of pharmaceutical applications including anticancers, antihypertensives, antivirals. Synthesis and evaluation of nsubstituted imidazole.
A simple and efficient method enables the synthesis of nalkynylheteroarenes from 1,1dibromo1alkenes via a coppercatalyzed crosscoupling reaction. Imidazole is a heterocyclic aromatic organic compound. In conclusion, novel biginelli dihydropyrimidinone derivatives containing imidazole moiety 115 were synthesized efficiently in good yield with a simple method, consisting of three components in a single pot. It is a benzimidazole and a polycyclic heteroarene. Look for imidazole and benzimidazole synthesis pdf ebook search. Almohammed 1, yatimah alias 1, zanariah abdullah 1,2, raied m. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has nonadjacent nitrogen atoms. Methods for synthesis of benzimidazole derivatives 22komal p et al.
Synthesis and antibacterial evaluation of some novel imidazole and benzimidazole sulfonamides nassir n. Imidazole and benzimidazole synthesis issn 1, grimmett, m. May 15, 2010 benzimidazole and imidazole inhibitors of histone deacetylases. Configurational isomers cis and trans of imidazole or benzimidazole modified cyclotriphosphazenes 3a, 4a or 3b, 4b were designed, synthesized and investigated as fluorescent probes for metal ions. It is a pharmacophore and a privileged structure in medicinal chemistry. Benzimidazole ring numbering and carbene center orbitals 3 figure 5.
Compounds 4144 were prepared by the reaction of imidazole 27 or 28 with dibromoalkanes in presence of nah and tbab in thf scheme 6. Khabnadideh s, rezaei z, khalafinezhad a, pakshir k, roosta a, baratzadeh z. Design and synthesis of imidazole and benzimidazole deerivatives as antifungal agents. Imidazole refers to the parent compound c3h4n2, while imidazoles are a class of heterocycles with similar ring structure but varying substituents. A simple and efficient preparation of 1substituted 1hazoles imidazole and benzimidazole has been developed, which involves a selective hofmanntype elimination of the 2cyanoethyl group from the azolium salts obtained by the reaction of halides with 1h imidazole 1propanenitrile and 1h benzimidazole 1propanenitrile. Imidazole and benzimidazole derivatives as chemotherapeutic agents volume. Nitrogencontaining heterocyclic compounds such as imidazole and benzimidazole form a framework of the important class of pharmacophores. Get it now imidazole and benzimidazole synthesis free pdf ebook. The systemic name for the compound is 1, 3diazole, one of the annular n. A welldefined nhcpdiiim complex enables a facile and alternative methodology for the direct ch bond arylation of benzimidazoles with heteroaryl chlorides. Benzimidazoles are a class of heterocyclic, aromatic compounds which share a fundamental structural characteristic of sixmembered benzene fused to fivemembered imidazole moiety. Taha 3 and aidil abdul hamid 4 1 chemistry department, faculty of.
Synthesis and optical properties of imidazole and benzimidazole based fused. It brings together the multitude of synthesis of the imidazole ring in a systemic way interms of specific bond formation, and recommends the most attractive synthetic approaches. Imidazole and benzimidazole synthesis 1st edition elsevier. Synopsis imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. Imidazolebenzimidazolemodified cyclotriphosphazenes as. They have attracted the attention of many researchers as their derivatives astemizole, mebendazole, enviroxime, carbendazime have been widely used and also commercialized 6, 7. Information on the synthesis, properties, and chemical transformations of imidazole noxides that are aromatic in nature is correlated. Imidazole is an organic compound with the formula c 3 n 2 h 4. Due to their special structural features and electronrich environment, imidazole and benzimidazole containing drugs bind to a variety of therapeutic targets, thereby exhibiting a broad spectrum of bioactivities. The reaction, shown below, produces imidazole when r 1 r 2 r 3 hydrogen. Synthesis methods of the benzimidazoles have been extensively summarized in previous studies, published by wright and preston. Imidazole is an entity which has interesting physical and chemical properties, in the present article focus lies on analysis of these properties which in turn may be exploited for different pharmacological activities, like compounds having a 3,4,5trimethoxyphenyl ring linked to either n1 or c4 position of the imidazole. Synthesis and antibacterial evaluation of some novel. The only book in print dealing specifically with this topic.
Benzimidazole 2 has a benzene ring fused in the 4,5positions of an imidazole ring. Imidazole and benzimidazole synthesis issn 1, grimmett. Synthesis and antifungal activity of benzimidazole. Herein, we focus on the chemical and physical properties of benzimidazole and its derivatives used for the synthesis of supramolecular materials. It is a tautomer of a 4h benzimidazole, a 2h benzimidazole and a 3ah benzimidazole. Here now, news for you imidazole and benzimidazole synthesis free ebooks in pdf. A useful reference for possible student experiments, starting materials for projects, and general information about heterocyclic ring construction. This book surveys the known methods of synthesis and ring modification and presents recommendations for the most attractive synthetic approaches. Imidazole can be synthesized by the photolysis of 1vinyltetrazole. In order to simplify the discussion around imidazole but is exactly the same with nitrogenbased heterocycles with more than one nitrogen, we refer to pyridinelike and.
Baran, richter essentials of heterocyclic chemistryi heterocyclic chemistry o s n n h n h n h o o n o n s n n h n n h hn n h n n h n n h h o n n h o h s n s s h n n n o o n n h h n n n n ss n n n s n n o n n n h nn s furan pk a. Imidazole and benzimidazole synthesis best synthetic methods. This book surveys the known methods of synthesis and ring. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It brings together the multitude of synthesis of the imidazole ring in a systemic way interms of specific bond formation, and recommends the most attractive synthetic. Ross grimmett, is published by academic press as part of their best synthetic methods series and subseries that deals with key systems and functional groups. The imidazole 4,5dicarboxylic acid is divided into two portions. The design and modification of benzimidazole opens the scope of the diversity of structures different sizes and morphologies that can be built. The molecules 1 and 2 are numbered as depicted on the structures. Imidazole and benzimidazole synthesis best synthetic. Synthesis of imidazole in this scheme, the synthesis of imidazole is carried out by refluxing 9, 10phenenthraquinone with aryl aldehyde, primary amines and ammonium acetate in the presence of glacial acetic acid in round bottom flask for 3 hrs. The partially and fully reduced derivatives of imidazole are variously designated as 2imidazoline 3, 3imidazoline 4, 4imidazoline 5 and imidazolidine 6. Benzimidazole, green synthesis, biological activity, 2arylbenzimidazole, 2aminobenzimidazole, 2alkylarylthiobenzimidazole. Basic strength and electronic structure the benzimidazoles are predominantly basic compounds having the ability to form salts with acids.
Synthesis of novel imidazole compounds and evaluation of. Synthesis and medicinal applications of benzimidazoles. This book chapter mainly discussed recent synthetic methods developed for the benzimidazole derivatives and their pharmacological properties exemplified on several derivatives. In the synthesis of substituted imidazole derivatives reported for sharma d. Synthesis of various substituted imidazole,benzimidazole, benzoxazole, tetrazole. The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substituted benzimidazole 2thiols 4ac followed by successive. Due to their special structural features and electronrich environment, imidazole and benzimidazole containing drugs bind to a variety of therapeutic targets, thereby exhibiting a broad spectrum of. This ring system is present in important biological building blocks such as histidine and histamine. Synthesis of nheterocycles benzofused nheterocycles synthesis of benzimidazoles. Dec 31, 2015 imidazole and benzimidazole rings are the most important nitrogencontaining heterocycles, which are widely explored and utilized by the pharmaceutical industry for drug discovery. The benzimidazole contains a phenyl ring fused to an imidazole ring, as indicated in the structure for benzimidazole figure 4. Imidazole, antimalarial antibacterial, anticancer, antifungal. The starting material enaminone was synthesized by reacting imidazole acetophenone with dimethylforamide dimethylacetal dmfdma under solventfree condition.
Synthesis and pharmacological profile of benzimidazoles. Imidazole and benzimidazole synthesis free saves of books in pdf format. In terms of the imidazole ring imidazole, 2methyl imidazole or 2ethyl imidazole, and benzimidazole, imidazolium salt hybrids 5059 with imidazole ring displayed weak cytotoxic activities. Nowadays it is a moiety of choice which possesses many pharmacological properties extensively explored with a. Synthesis, chemistry and therapeutic approaches of. Purines, structural relatives of benzimidazoles 1 figure 3. Supramolecular assembly of benzimidazole derivatives and. There are no really general oways of synthesizing imidazoles and it is invariably necessary to consider a number of divergent methods whenever a synthesis is contemplated n h n n n h h n n h h ring formation. Benzoxazole natural products and medicinalagrochemical applications of benzoxazoles.
745 1315 151 1579 133 126 336 1313 618 1077 1069 330 177 438 667 1111 1048 789 168 811 390 262 1437 1380 894 837 201 1367