A simple, two-step synthesis of 3-iodoindoles

Amjad, Muhammad; Knight, David W.

doi:10.1016/j.tetlet.2003.10.207

Cited by 161 publications

(38 citation statements)

References 14 publications

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“…由于呋喃结构 2 位的活性较高, 使用通常碘化的方法只能在 2 位引入碘原子, 因此该方法提供了一种合成 3-位碘代呋喃很好的策略 [55] . [59] . Oxone 是商品化的过硫酸氢钾复合盐, 也是有机合成中经常使用的一类氧化剂.…”

Section: Lewis 酸催化剂unclassified

Recent Advances in Iodine-Mediated Organic Reactions

Zhao¹,

Gao²,

Chang³

et al. 2014

Chin. J. Org. Chem.

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As one of simplest chemical reagents, iodine has promoted diverse organic transformations, which have attracted much attention in recent years. The present review summarizes three basic chemical features of iodine in organic synthesis: the oxidative reactivity, the acidic reactivity and the electrophilic reactivity, along with the introduction of corresponding representative examples. Furthermore, the iodine-catalyzed reactions involed in the synthesis of heterocycles, organic coupling reactions, the C-H functionalization, and other applications are also presented in this review.

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Section: Lewis 酸催化剂unclassified

Recent Advances in Iodine-Mediated Organic Reactions

Zhao¹,

Gao²,

Chang³

et al. 2014

Chin. J. Org. Chem.

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“…Sono- gashira coupling of o-haloanilines with terminal alkynes followed by cyclization of the resulting 2-alkynylanilines in the presence of various reagents (e.g., Pd catalysts, metal alkoxides, halides, or Lewis acids). [41][42][43][44][45] The N-methanesulfonyl derivative of 2-iodoaniline 21a provided better results than N-trifluoroacetyl derivatives 21b, although the unprotected indoles 22b were obtained directly in the second case (Scheme 7).…”

Section: Synthesis Of Indolesmentioning

confidence: 99%

Palladium-Catalyzed Alkynylation of Aryl and Hetaryl Halides: A Journey from Conventional Palladium Complexes or Salts to Palladium/Carbon

Pal¹

2009

Synlett

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Palladium-catalyzed alkynylation of aryl and hetaryl halides has found wide application in the areas of synthetic, heterocyclic, and medicinal chemistry. Attempts to introduce the stable and potentially recyclable palladium/carbon has provided an attractive alternative to the homogeneous palladium catalytic process. The present article provides a personal account of the outcome of the use of conventional palladium catalysts versus palladium/carbon, especially under Sonogashira conditions.

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“…23 This compound was cyclized upon treatment with iodine and potassium carbonate in acetonitrile to afford the protected indole derivative 15 . 24 Removal of tosylate protecting group was achieved in 86% yield by heating a solution of 16 at 60–70 °C in THF in the presence of tetra- n -butylammonium fluoride. In the absence of iodine or NIS, compound 16 can be purified by column chromatography and is sufficiently stable for storage.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and DNA-binding affinity studies of glycosylated intercalators designed as functional mimics of the anthracycline antibiotics

2009

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Anthracycline antibiotics such as daunomycin (Dauno) and doxorubicin (Dox) are well-known clinically used cancer chemotherapeutics, which, among other mechanisms, bind to DNA, thereby triggering a cascade of biological responses leading to cell death. However, anthracyclines are cardiotoxic, and drug resistance develops rapidly, thus limiting their clinical use. We report here the synthesis and DNA-binding affinity of a novel class of functional anthracycline mimetics consisting of an aromatic moiety linked to a carbohydrate (1–12). In the targets, the aromatic core consists of a 2-phenylbenzo[b]furan-3-yl, 2-phenylbenzo[b]thiophen-3-yl, 1-tosyl-2-phenylindol-3-yl, or 2-phenylindol-3-yl group that is bound to one of three aminosugars (daunosamine, acosamine, or 4-amino-2,3,4,6-tetradeoxy-α-L-hexopyranoside) via a propargyl linker. The DNA binding affinity of these twelve compounds has been evaluated by using both direct and indirect fluorescence measurements. Compared to Dauno and Dox, the DNA binding affinity of these analogues is weaker. However, both aromatic and aminosugar motifs are critical to DNA binding, with more influence coming from the structural features of the aromatic portion.

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A simple, two-step synthesis of 3-iodoindoles

Cited by 161 publications

References 14 publications

Recent Advances in Iodine-Mediated Organic Reactions

Recent Advances in Iodine-Mediated Organic Reactions

Palladium-Catalyzed Alkynylation of Aryl and Hetaryl Halides: A Journey from Conventional Palladium Complexes or Salts to Palladium/Carbon

Synthesis and DNA-binding affinity studies of glycosylated intercalators designed as functional mimics of the anthracycline antibiotics

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