Electrochemical reduction of o-nitrophenylthioacetic derivatives. Production of 2H-1,4-benzothiazines

Sicker, Dieter; Hartenstein, H.; Mouats, Chabane; Hazard, R; Tallec, A.

doi:10.1016/0013-4686(95)00083-q

Cited by 12 publications

(8 citation statements)

References 9 publications

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“…However, in this case, 20% of 7‐ethoxy derivative was formed as a by‐product. Finally, substituting 0.5 M H 2 SO 4 for 1.0 M NH 4 Cl/NH 3 gave rise to 2 H ‐4‐hydroxy‐1,4‐benzthiazin‐3‐one in quantitative yield . Similarly, 2 H ‐4‐hydroxy‐1,4‐benzoxazin‐3‐one was obtained from a mixture of sulfuric acid (0.5 M) and ethanol (1:1 v/v) in quantitative yield .…”

Section: Nitro Derivativesmentioning

confidence: 93%

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

2020

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In this review,t he versatile and rich chemistry for the electrochemical reductiono fs ubstrates involving N À Ob onds is surveyed. By the cathodic treatment of nitro,n itroso and other oxygenated organic nitrogen substrates,v ersatile andr eactive intermediates are formed which can be subsequently converted to high value-added products. In many examples,n itrogen heterocycles are selectively formed, but, also depending on the electrolytic conditions, free oximes,n itrones,a mines and other entities can be obtained as well. Ther ecent decades have witnessed twom ajor advances-(i)g oing directly to more complext arget molecules and (ii)c onductingt he electrolysesi nm uch simpler set-ups.Both improvements make the cathodic access of the target compoundsm uch more practical and scalable. 1I ntroduction 2N itro Derivatives 2.1 IntermolecularReactions 2.2 IntramolecularReactions:Synthesis of Heterocycles 3O ximes 4O ther Functionalities 5C onclusions

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Section: Nitro Derivativesmentioning

confidence: 93%

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

2020

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“…Theoratically, the average number of electrons required to reduce one molecule of substrate was essentially 4. 70 Recently, Peters and co-workers developed an efficient method for the electrosynthesis of 1H-indoles 225 from onitrostyrene 224 (Scheme 76). 71 These electrochemical reductions were carried out at carbon cathodes in DMF with tetramethylammonium tetrafluoroborate (TMABF 4 ) as the supporting electrolyte.…”

Section: Electroreductive Intramolecular Coupling Of Cyclicmentioning

confidence: 99%

“…Tallec and co-workers reported that o -nitrophenoxyacetic acid or its methyl ester ( 218a – 218b ) and 2-( o -nitrophenylthio)-acetic acid or its methyl ester ( 219a – 219b ) could be reduced to form phenylhydroxylamines ( 220 – 221 ) under electrochemical conditions, which then underwent cyclization to give 4-hydroxy-2 H -1,4-benzoxazin-3(4 H )-one 222 and 4-hydroxy-2 H -1,4-benzothiazin-3(4 H )-one 223 (Scheme ). Theoratically, the average number of electrons required to reduce one molecule of substrate was essentially 4 …”

Section: Intramolecular Cyclizationmentioning

confidence: 99%

Use of Electrochemistry in the Synthesis of Heterocyclic Structures

2017

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The preparation and transformation of heterocyclic structures have always been of great interest in organic chemistry. Electrochemical technique provides a versatile and powerful approach to the assembly of various heterocyclic structures. In this review, we examine the advance in relation to the electrochemical construction of heterocyclic compounds published since 2000 via intra- and intermolecular cyclization reactions.

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“…For the preparation of heterocyclic compounds, see: Weinberg & Tilak (1982); Katritzky & Lagowski (1971); Sicker et al (1995). For bond lengths and angles in similar compounds, see: Cai et al (2011); Yakimanski et al (1997).…”

Section: Related Literaturementioning

confidence: 99%

“…The chemical reductions are not always selective and often lead to mixtures (Katritzky & Lagowski, 1971). In particular, the reduction of substituted nitrobenzenes with controlled potential can produce a number of heterocycles (Sicker et al, 1995).…”

Section: Sup-1mentioning

confidence: 99%

1-[3-(4-Nitrophenyl)propanoyl]urea acetic acid monosolvate

et al. 2011

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The title compound, C10H11N3O4·C2H4O2, was prepared by an electrochemical technique. In the crystal, acetic acid molecules are involved in hydrogen bonding to two separate propanoylurea molecules, acting as a donor in an O—H⋯O interaction and as an acceptor in two N—H⋯O interactions. The propanoylurea molecules interact with each other via N—H⋯O hydrogen bonds. C—H⋯O interactions also stabilize the crystal structure.

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Electrochemical reduction of o-nitrophenylthioacetic derivatives. Production of 2H-1,4-benzothiazines

Cited by 12 publications

References 9 publications

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

Use of Electrochemistry in the Synthesis of Heterocyclic Structures

1-[3-(4-Nitrophenyl)propanoyl]urea acetic acid monosolvate

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