Reaction of ?-deficient aromatic heterocycles with ammonium polyhalides III. Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides

Custelceanu, R.; Vlassa, M.; Silberg, Ioan A.

doi:10.1007/bf00807101

Monatsh Chem

1997

DOI: 10.1007/bf00807101

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Reaction of ?-deficient aromatic heterocycles with ammonium polyhalides III. Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides

R. Custelceanu

M. Vlassa

Ioan A. Silberg

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Cited by 6 publications

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“…In the course of our work toward the synthesis of oligo(phenylene ethynylene)diazonium salts, there has been a constant need for iodinated anilines. The mildest and most para selective procedures reported in the literature employ benzyltrimethyl ( 1 ) or benzyltriethylammonium ( 2 ) dichloroiodates in both free and polymer-supported form . Being fairly straightforward, the synthesis of the dichloroiodate 2 requires corrosive and moisture sensitive iodine monochloride and large amounts of organic solvents (dichloromethane and ethyl ether).…”

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Benzyltriethylammonium Dichloroiodate/Sodium Bicarbonate Combination as an Inexpensive, Environmentally Friendly, and Mild Iodinating Reagent for Anilines

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Tour

2001

Org. Lett.

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All reactions were performed under an atmosphere of nitrogen unless stated otherwise. Tetrahydrofuran (THF) was distilled from sodium benzophenone ketyl. Hexanes and dichloromethane were distilled under nitrogen. Anilines were commercial samples (Aldrich) used without additional purification.Silica gel plates were 250 µm thick, 40 F 254 grade from EM Science. Silica gel was grade 60 (230-400 mesh) from EM Science. 1 H and 13 C NMR spectra were obtained at 400 and 100 MHz, respectively. IR assignments have 2 cm -1 resolution.Benzyltriethylammonium dichloroiodate (2) from iodine. Commercial bleach (5.25% NaClO, 100 mL, 80 mmol) was added to iodine (20.32 g, 80 mmol), water (200 mL) and concentrated hydrochloric acid (100 mL) contained in an Erlenmeyer flask sitting in an ice bath at such a rate as to keep the temperature below 20 ºC. Toward the end of the bleach addition, the bleach was added dropwise until the endpoint manifested by the disappearance of the brown coloration of iodine was reached. Then, 10% aqueous NaI was added dropwise to restore the barely visible brown coloration and the resulting orange solution was gradually introduced into a solution of benzyltriethylammonium chloride (36.4 g, 160 mmol) in water (50 mL). The resulting light-yellow precipitate was collected by filtration, washed with water (100 mL, 3X)

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mentioning

confidence: 99%

Benzyltriethylammonium Dichloroiodate/Sodium Bicarbonate Combination as an Inexpensive, Environmentally Friendly, and Mild Iodinating Reagent for Anilines

and

Tour

2001

Org. Lett.

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Synthesis and Properties of Hydrazine‐Embedded Biphenothiazines and Application of Hydrazine‐Embedded Heterocyclic Compounds to Fluorescence Cell Imaging

et al. 2018

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Hydrazine-embedded unsubstituted butterflyshaped biphenothiazine and its sulfoxides were synthesized by dimerization of 1,9-dibromophenothiazine, which was prepared by realizing selective debromination at the 3,7positions of 1,3,7,9-tetrabromophenothiazine. cis/trans-Biphenothiazine sulfoxide was selectively prepared by changing the oxidation temperature to control the inversion rate of the butterfly shape of the intermediate. Their butterflyshapes, conformations, photophysical properties (UV-vis absorption, fluorescence), and redox properties were elucidated by X-ray analysis, DFT calculations, spectral and electrochemical measurements. Fluorescent hydrazine-embedded biphenothiazine sulfoxides and bicarbazoles were applied to cell imaging of HeLa cells. The bicarbazoles exhibited high fluorescence signals in the cells with low toxicity.[a] Prof.

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ChemInform Abstract: Reaction of π‐Deficient Aromatic Heterocycles with Ammonium Polyhalides. Part 3. Halogenation of Phenothiazin‐5‐oxide with Benzyltriethylammonium Polyhalides.

1997

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Reaction of π-Deficient Aromatic Heterocycles with Ammonium Polyhalides. Part 3. Halogenation of Phenothiazin-5-oxide with Benzyltriethylammonium Polyhalides.-The title reaction affords chloroand bromophenothiazines (III) and ( V) as well as a few unexpected products such as compounds (II), (IV), and (VI). A new charge-transfer complex of phenothiazine-5-oxide with bromine (VII) is reported. -(CUSTELCEANU, R.; VLASSA, M.; SILBERG, I. A.; Monatsh. Chem. 128 (1997) 8-9, 919-925; Dep. Org. Chem., Fac. Chem. Chem. Eng., Babes-Bolyai Univ., RO-3400 Cluj-Napoca, Rom.; EN)

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Reaction of ?-deficient aromatic heterocycles with ammonium polyhalides III. Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides

Cited by 6 publications

References 15 publications

Benzyltriethylammonium Dichloroiodate/Sodium Bicarbonate Combination as an Inexpensive, Environmentally Friendly, and Mild Iodinating Reagent for Anilines

Benzyltriethylammonium Dichloroiodate/Sodium Bicarbonate Combination as an Inexpensive, Environmentally Friendly, and Mild Iodinating Reagent for Anilines

Synthesis and Properties of Hydrazine‐Embedded Biphenothiazines and Application of Hydrazine‐Embedded Heterocyclic Compounds to Fluorescence Cell Imaging

ChemInform Abstract: Reaction of π‐Deficient Aromatic Heterocycles with Ammonium Polyhalides. Part 3. Halogenation of Phenothiazin‐5‐oxide with Benzyltriethylammonium Polyhalides.

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