Track topics on Twitter Track topics that are important to you
In a one-pot procedure, bromine less brominating reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been utilized as an efficient desulfurizing agent for the construction of a library of heterocycles containing N, O, and S starting from aryl/alkyl isothiocyanates. In this approach, aryl/alkyl isothiocyanate reacts with o-phenylenediamine (o-PD), o-aminophenol, and o-aminothiophenol to form their monothiourea which on desulfurization with EDPBT led to the formation of corresponding 2-aminobenzimidazoles, 2-aminobenzoxazoles, and 2-aminobenzothiazoles, respectively. An interesting regioselectivity was observed for unsymmetrical thiourea having a naphthyl moiety on the one side and an ortho amino or an ortho hydroxy phenyl group on the other side giving a completely different product which is mainly dependent on the nature of the nucleophiles (-OH or -NH(2)). Further, the bis-thioureas resulted from the aliphatic 1,2-diamine with 2 equiv of aryl isothiocyanates on treatment with EDPBT gave imidazolidenecarbothioamides, whereas bis-thioureas resulted from aromatic 1,2-diamine yielded benzimidazoles with concurrent expulsion of an isothiocyanate unit. This method is simple and applied to various substrates which are amenable to bromination that reveals the desulfurizing ability of EDPBT predominating over its brominating ability. Finally, the spent reagent EDPDB can be recovered, regenerated, and reused without any loss of activity.
Department of Chemistry, Indian Institute of Technology Guwahati, Assam 781 039, India.
This article was published in the following journal.
Name: Journal of combinatorial chemistry
An unprecedented Rh(III)-catalyzed annulation of various benzamides and acrylamides with quinone monoacetals was developed for the facile and efficient one-pot synthesis of bridged nine-membered benzo...
Diverse general, high yield routes for novel thieno- fused five and six membered nitrogen and oxygen heterocycles such as thieno[3,2-b]pyrroles, thieno[3,2-b]furans, thieno[3,2-b]indoles, thieno[3,2-b...
2,3-bis(dimethylamino)-substituted B2N2C2 heterocycles underwent selective dimethylamino/hydride exchange with either one or two equivalents of BH3∙SMe2 to yield the corresponding cyclic monohydrido...
Incorporating the silicon element into bioactive organic molecules has received increasingly attention in medicinal chemistry. Moreover, organosilanes are valuable synthetic intermediates for fine che...
N-Phenyltrifluoroacetimidoyl chloride (PTFAI-Cl) is a reagent widely used for the preparation of glycosyl N-phenyltrifluoroacetimidates. However, the most commonly applied method requires carbon tetra...
Cholesterol is the precursor of glucocorticoids, mineralocorticoids and sex steroids. Both adrenal and non-adrenal (ovarian + testicular) all steroid hormones are primarily synthesized usi...
Collagen synthesis is depressed systemically in the immediate postoperative period. Arginine, zinc and vitamin C impact collagen synthesis. The aim of this study is to investigate the eff...
The present proposal is designed to examine the effect of carbohydrate and protein co-ingestion on muscle protein synthesis during endurance type exercise activities. We hypothesize that m...
The aim of the present study is to investigate the effect of added protein+leucine or caffeine to 1.2 g/kg/h CHO on the rate of post-exercise muscle glycogen re-synthesis in healthy, recre...
The primary purpose of the study is to evaluate the therapeutic efficacy and safety of cholic acid in subjects with identified inborn errors of bile acid synthesis.
Six-membered heterocycles containing an oxygen and a nitrogen.
Unsaturated azacyclopropane compounds that are three-membered heterocycles of a nitrogen and two carbon atoms.
Compounds with a 5-membered ring of four carbons and an oxygen. They are aromatic heterocycles. The reduced form is tetrahydrofuran.
Compounds based on a seven-membered ring fused to a five-membered ring. Heat can rearrange them to NAPHTHALENES which have two fused six-membered rings. They are similar to guaiazulenes which are SESQUITERPENES with a six-membered ring fused to a five-membered ring.
An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.