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Iodine/palladium approaches to the synthesis of polyheterocyclic compounds.

ABSTRACT: A simple, straightforward strategy for the synthesis of polyheterocyclic compounds (PHCs) is reported, which involves iterative cycles of palladium-catalyzed Sonogashira coupling, followed by iodocyclization using I(2) or ICl. A variety of heterocyclic units, including benzofurans, benzothiophenes, indoles, and isocoumarins, can be efficiently incorporated under mild reaction conditions. In addition, variations of this strategy afford a variety of linked and fused PHCs.

SUBMITTER: Mehta S

PROVIDER: S-EPMC2832103 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Iodine/palladium approaches to the synthesis of polyheterocyclic compounds.

Mehta Saurabh S Larock Richard C RC

The Journal of organic chemistry 20100301 5

A simple, straightforward strategy for the synthesis of polyheterocyclic compounds (PHCs) is reported, which involves iterative cycles of palladium-catalyzed Sonogashira coupling, followed by iodocyclization using I(2) or ICl. A variety of heterocyclic units, including benzofurans, benzothiophenes, indoles, and isocoumarins, can be efficiently incorporated under mild reaction conditions. In addition, variations of this strategy afford a variety of linked and fused PHCs. ...[more]

PMID: 20121269

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Project description:A human's diet should be diverse and rich in vitamins, macro- and microelements essential for the proper functioning of the human body. Globally, a high percentage of the human population suffers from malnutrition, deficiencies of nutrients and vitamins also known as the problem of hidden hunger. This problem it is not only common in poor countries, but also occurs in developed countries. Iodine is a nutrient crucial for the proper functioning of the human and animal body. For plants, it is referred to as a beneficial element or even a microelement. The design of the biofortification experiment was determined on the basis of the interaction of iodine and vanadium (synergistic interaction in marine algae), where vanadium-dependent iodoperoxidase catalyzes apoplastic oxidation of iodine, resulting in high efficiency of iodine uptake and accumulation in brown algae (Laminaria digitate). Three independent experiments (Exp.) were carried out with the foliar application of vanadium (V) and iodine (I) compounds. The main differences between the experiments with the adapted proper corn biofortification method were the different application stage between the individual experiments, the application intervals and the dose of the iodine-vanadium compound. In each experiment, the accumulation of iodine and vanadium in the grain was several times lower than in the leaves. The combination iodine and vanadium significantly increased the accumulation of iodine in the grain in the case of applying V with inorganic iodine compounds, and a decrease in the accumulation of I after applying V with organic iodine compound -especially in Exp. No. 3. In grain, the highest content of I-, IO3- was in combination with the application of 2-iodobenzoic acid (products of its metabolism). In most of the tested combinations, vanadium stimulated the accumulation/synthesis of exogenous/endogenous 5-iodosalicylic acid (5ISA) and 2-iodobenzoic acid (2IBeA), respectively, and decreased the content of 2,3,5-triiodobenzoic acid (2,3,5-triIBeA) in leaves and grains. The tested compounds I and V and the combinations of their application had a diversified effect on the vitamin C content in the grains. Vanadium in the lower dose of 0.1 µM significantly increased the sugar content in the grain.

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Iodine/palladium approaches to the synthesis of polyheterocyclic compounds.

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Iodine/palladium approaches to the synthesis of polyheterocyclic compounds.

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