- Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
- Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
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- Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst
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Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.
- Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias
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supporting information
p. 20543 - 20550
(2021/08/12)
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- Aromatic Chlorosulfonylation by Photoredox Catalysis
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Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.
- Májek, Michal,Neumeier, Michael,Jacobi von Wangelin, Axel
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p. 151 - 155
(2017/01/17)
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- Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties
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A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 γ1/4g/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.
- Wang, Bao-Lei,Shi, Yan-Xia,Zhang, Shu-Jun,Ma, Yi,Wang, Hong-Xue,Zhang, Li-Yuan,Wei, Wei,Liu, Xing-Hai,Li, Yong-Hong,Li, Zheng-Ming,Li, Bao-Ju
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p. 167 - 178
(2016/04/26)
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- Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids
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A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.
- Debergh, J. Robb,Niljianskul, Nootaree,Buchwald, Stephen L.
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supporting information
p. 10638 - 10641
(2013/08/23)
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- A new effective synthesis of arene mono- and disulfonyl chlorides
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Arene mono- and disulfonyl chlorides have been easily synthesized starting from the corresponding anilines via aqueous oxidative chlorination of S-aryl O-ethyl dithiocarbonates intermediates, aryl methyl sulfides, or from arenethiols. Georg Thieme Verlag Stuttgart.
- Barbero, Margherita,Bazzi, Stefano,Cadamuro, Silvano,Dughera, Stefano,Magistris, Claudio,Venturello, Paolo
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supporting information; experimental part
p. 1803 - 1806
(2010/10/20)
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- Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists
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The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.
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- Polymer electrolyte and process for producing the same
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A polymer electrolyte having, in a main chain, a structural unit represented by the following formula (1):-[Ar1-(SO2-N-(X+)-SO2-Ar2)m-SO2-N-(X+)-SO2-Ar1-O]- wherein Ar1 and Ar2 independently represent a divalent aromatic groups, m represents an integer of 0 to 3, and X+ represents an ion selected from hydrogen ion, an alkali metal ion and ammonium ion, which is excellent in proton conductivity, thermal resistance and strength. The polymer electrolyte is soluble in solvents and has excellent film forming property and recycling efficiency.
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- Preparation of 2-chloro-5-methyl-pyridine
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A process for the preparation of 2-chloro-5-methylpyridine of the formula STR1 which comprises reacting 3-methyl-pyridine-1-oxide of the formula STR2 with a chlorinating agent of the formula STR3 in which R1 represents alkyl, halogenoalkyl, cycloalkyl, optionally substituted aryl, NR2 R3 or OR4 in which R2 and R3 individually represent alkyl, cycloalkyl or aryl or together represent alkanediyl or oxaalkanediyl and R4 represents alkyl, cycloalkyl or optionally substituted aryl, in the presence of a basic organic nitrogen compound and in the presence of a diluent at a temperature between about -20° C. and +150° C.
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- Preparation of 4,4' dichlorodiphenyl sulfone
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A process for the preparation of 4,4-dichlorodiphenyl sulfone by heating a mixture of (a) chlorobenzene, (b) chlorosulfonic acid or sulfur trioxide, and (c) thionyl chloride or phosgene to temperatures up to 220° C., more than the stoichiometric amount (based on the amount of chlorobenzene) of chlorosulfonic acid or sulfur trioxide and less than the stoichiometric amount of thionyl chloride or phosgene being employed.
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- SYNTHESIS OF N-(2-CHLOROPHENYLSULFONYL)-N'-(4-METHOXY-6-METHYL-1,3,5-TRIAZIN-2-YL)-UREA WITH A RADIOACTIVE LABEL
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Methods for the introduction of a radioactive 13C label into N-(2-chlorophenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea, which has herbicidal activity, are described.
- Sokolova, G. D.,Khokhlov, P. S.
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p. 547 - 550
(2007/10/02)
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- Process for the preparation of N'-sulphonyl- and N',N"-bis-sulphonyl-guanidine derivatives
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A process for the preparation of a guanidine derivative of the formula STR1 in which R1 represents hydrogen or the radical R5 --S(O)m --, m represents the numbers zero, 1 or 2 and R5 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl, R2 represents a six-membered aromatic heterocyclic structure which contains at least one nitrogen atom and is substituted, and R8 represents an optionally substituted radical from the series comprising C1 -C6 -alkyl, alkenyl, alkinyl, cycloalkyl, phenylalkyl and aryl, which comprises reacting a guanidine derivative of the formula STR2 with one or two molar equivalent(s), respectively, of a halogen/sulphur compound of the formula in which X1 represents fluorine, chlorine or bromine. The compounds are herbicidally active.
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- Sulphonyliso(thio)urea derivatives and herbicidal use thereof
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The invention relates relates to new sulphonyliso(thio)-urea derivatives of the general formula (I) STR1 in which R1 represent an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl R2 represents an optionally substituted and/or optionally fused 6-membered aromatic heterocyclic radial containing at least one nitrogen atom, R3 represents an optically substituted aromatic or heteroaromatic radical, X represents oxygen or sulphur and M represents hydrogen or an equivalent of a metal, and adducts of compounds of the formula (I) with strong acids, processes for their prepartion, and their use as herbicides.
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- Substituted guanidine derivatives
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A plant growth regulating compound of the formula STR1 in which R2 is an optionally substituted nitrogen heterocyclic radical, R3 is hydrogen, alkyl, cycloalkyl, alkenyl, alkinyl or aralkyl, and R4 is hydrogen, or if R3 is not hydrogen R4 may be hydroxyl or a variety of radicals, or R3 and R4 together may form a ring, or an acid adduct thereof.
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- N'-(substituted-pyrimidin-2-yl)-N"-amino-N"'-(substituted-benzenesulphonyl)-guanidines as herbicides
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Herbicidally active guanidine derivatives of the formula STR1 in which m represents the numbers zero, 1 or 2, R5 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl, R2 represents a pyrimidin-2-yl radical which is substituted by halogen, amino, cyano or formyl and/or by optionally substituted radicals from the series comprising alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl and alkoxycarbonyl, R3 represents hydrogen, an optionally substituted radical from series comprising alkyl, cycloalkyl, alkenyl, alkinyl and aralkyl, R9 represents hydrogen or optionally substituted alkyl and R10 represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, heteroaryl, alkyl- or alkoxycarbonyl and alkyl- or arylsulphonyl, or R9 and R10 together represent alkanediyl which is optionally interrupted by an oxygen atom; and M represents hydrogen, one equivalent of a metal, or an ammonium radical which is optionally substituted by alkyl, alkenyl, alkinyl and/or aralkyl, or--in the case in which M is bonded to the same nitrogen atom as R2 --also represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl and aralkyl, or acid adducts thereof.
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- N'-(substituted-1,3,5-triazin-2-yl)-N"-substituted-N",N"'-bis-(substituted-benzenesulphonyl)-guanidines as herbicides
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Herbicidally active novel N,N'-bis-sulphonyl guanidines of the formula STR1 in which M is hydrogen, a metal or an ammonium radical, and R4, R5, R40 and R41 are various organic radicals.
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- N'-(substituted-1,3,5-triazin-2-yl)-N"-amino-N"'-(substituted-benzenesulphonyl)-guanidines as herbicides
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A selective herbicide of the formula STR1 in which m is 0, 1 or 2, R5 is an organic radical, R3 is hydrogen or an organic radical, R9 is hydrogen or an optionally substituted alkyl radical, R10 is an organic radical or forms a ring with R9, R40 and R41 are alkyl or alkoxy, and M is hydrogen or a metal or ammonium radical, or an acid adduct thereof.
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- Preparation of sulphonyliso(thio)ureas and sulphonylisoureas
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A process for the preparation of a sulphonyliso(thio)urea of the formula STR1 in which R1 represents an optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl, R2 represents an optionally substituted and/or optionally fused, six-membered aromatic heterocycle containing at least one nitrogen atom, R3 represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl and aralkyl, and Q represents oxygen or sulphur, comprising reacting a sulphonylguanidine of the formula STR2 in which R4 represents an optionally substituted hydrocarbon radical, with a compound of the formula at a temperature between 0° C. and 150° C. The products are known herbicides.
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- N'-(substituted-pyrimidin-2-yl)-N"-substituted-N",N"'-bis-(substituted-benzenesulphonyl)-guanidines as herbicides
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Guanidine derivatives of the formula STR1 in which R2 represents a six-membered aromatic heterocyclic structure which contains at least one nitrogen atom and is substituted by halogen, amino, cyano or formyl and/or by optionally substituted radicals from the series comprising alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl and alkoxycarbonyl, and/or is optionally fused, R3 represents hydrogen, an optionally substituted radical from the series comprising alkyl, cycloalkyl, alkenyl, alkinyl and aralkyl, or the radical --S(O)n --R6, the other radicals can have varied meanings, and acid adducts and salts thereof, which possess herbicidal and plant growth regulating activity.
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