Preparation of monohalopyrroles

Aiello, Enrico; Dattolo, Gaetano; Cirrincione, Girolamo; Almerico, Anna Maria; D'Asdia, Isabella

doi:10.1002/jhet.5570190460

Cited by 27 publications

(16 citation statements)

References 13 publications

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“…Notably, however, treatment of 1-alkylpyrroles with NCS in chloroform with or without NaHCO 3 leads instead to introduction of the N-succinimide moiety at C2 [230]. Application of N-halosuccinimides in DMF provides convenient access to a series of 2,5-disubstituted or 2,4,5-trisubstituted 3-chloro-, 3-bromo-and 3-iodopyrrole derivatives [231]. The selective rearrangement of 1-benzyl-2,5-dibromopyrrole (150) with p-toluenesulfonic acid into the product 151 (Scheme 4.47) is also worth mentioning in this context [232].…”

Section: Halogenationmentioning

confidence: 98%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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Section: Halogenationmentioning

confidence: 98%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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“…Since halogenation with N-halosuccinimides in dimethylformamide gave excellent yields in monohalopyrroles, 7 we chose this reaction to protect the 3 position of the indole nucleus. Thus, compound 6a was brominated with NBS in dimethylformamide to give the corresponding 3-bromo-2-(2-nitrophenyl)indole (8) in quantitative yield.…”

Section: Chemistrymentioning

confidence: 99%

Derivatives of the New Ring System Indolo[1,2-c]benzo[1,2,3]triazine with Potent Antitumor and Antimicrobial Activity

Cirrincione¹,

Almerico²,

Barraja³

et al. 1999

J. Med. Chem.

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Derivatives of the new ring system indolo[1,2-c]benzo[1,2,3]triazine 5 were synthesized by diazotization of substituted 2-(2-aminophenyl)indoles followed by an intramolecular coupling reaction of the diazonium group with the indole nitrogen. To obtain the indolobenzotriazine system it was necessary to protect the 3 position of the indole nucleus to avoid cyclization into the indolo[3,2-c]cinnoline system 4. Indolobenzotriazines 5a-g were evaluated in vitro for antitumor activity against a panel of leukemia-, lymphoma-, carcinoma-, and neuroblastoma-derived cell lines. Some compounds inhibited the proliferation of T and B cell lines at submicromolar concentrations, whereas their activity against solid tumor cell lines was in the micromolar range. When evaluated for their antifungal potential 5a,d inhibited some of the fungi tested, although at concentrations very close to those inhibiting the proliferation of human cells. On the contrary, all indolobenzotriazines proved fairly potent and selective inhibitors of Streptococcus and Staphylococcus. In particular 5b,c,g were up to 80 times more potent than the reference drug streptomycin and inhibited the growth of the above Gram-positive bacteria at concentrations far lower than those cytotoxic for animal cells.

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“…However, it is well known that entanglement properties of a bipartite system depend on the dimensionality of the underlying Hilbert space [12,13], therefore the "measurement-induced" reduction from 4 × N A × N B to 4 dimensions, may change the observed properties of the system. The problem of the determination of the effective dimensionality of the scattered pair state, is at present under investigation in our group [15].…”

Section: A Two-photon Scattering Matrixmentioning

confidence: 99%

“…In this case a traditional Bell-violation measurement setup may fail to reveal a maximal violation of the Bell-CHSH inequality. However, the detailed investigation of the entanglement properties of this kind of high-dimensional scattered photon-pair [12,13,14], is left to a forthcoming paper [15]. This paper is structured as follows.…”

Section: Introductionmentioning

confidence: 99%

Intrinsic entanglement degradation by multimode detection

Aiello

Woerdman

2004

Phys. Rev. A

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Relations between photon scattering, entanglement and multi-mode detection are investigated. We first establish a general framework in which one-and two-photon elastic scattering processes can be discussed, then we focus on the study of the intrinsic entanglement degradation caused by a multi-mode detection. We show that any multi-mode scattered state cannot maximally violate the Bell-CHSH inequality because of the momentum spread. The results presented here have general validity and can be applied to both deterministic and random scattering processes.

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Preparation of monohalopyrroles

Abstract: Monobromo‐, monochloro‐ and monoiodopyrroles are obtained in excellent yields by using N‐halosuccinimides in dimethylformamide as halogenating agents.

Cited by 27 publications

References 13 publications

Five‐Membered Heterocycles: Pyrrole and Related Systems

Five‐Membered Heterocycles: Pyrrole and Related Systems

Derivatives of the New Ring System Indolo[1,2-c]benzo[1,2,3]triazine with Potent Antitumor and Antimicrobial Activity

Intrinsic entanglement degradation by multimode detection

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