Reactions of N-(Polychloroethylidene)arene-and - trifluoromethanesulfonamides with indoles

Kondrashov, E. V.; Rudyakova, E. V.; Розенцвейг, И. Б.; Ushakova, I. V.; Rozentsveig, G. N.; Savosik, V. A.; Chernyshev, K. A.; Krivdin, Leonid B.; Levkovskaya, G. G.

doi:10.1134/s1070428008010107

Cited by 9 publications

(5 citation statements)

References 6 publications

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“…In a series of works, Rozentsveig et al have shown it to react with 1,2-dichloroethylene, − trichloroethylene, , and vinylidene chloride to give CF 3 SO 2 NCHCHCl 2 , CF 3 SO 2 NCHCCl 3 , and CF 3 SO 2 NHCH 2 CCl 3 , respectively. A highly electrophilic CN bond adds various O- (water, methanol, p -nitrophenol), N- (PhSO 2 NH 2 , triflamide, acrylamide), and C-nucleophiles (phenol, thiophene, indoles, pyrazoles). − With tribromoethylene, depending on the reaction conditions, N , N -dichlorotriflamide gives either CF 3 SO 2 NCHCBr 2 Cl (at <40 °C) or its 1:1 mixture with CF 3 SO 2 NCHCBr 3 (when the reaction mixture is allowed to warm up to 100 °C) …”

Section: Trifluoromethanesulfonamides (Triflamides)mentioning

confidence: 99%

Trifluoromethanesulfonamides and Related Compounds

2012

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Section: Trifluoromethanesulfonamides (Triflamides)mentioning

confidence: 99%

Trifluoromethanesulfonamides and Related Compounds

2012

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“…35 We succeeded to decrease the amounts of the solvent (by 2-3 times) and alkali (KOH) (by 1.5 used) by using more available NaOH as a base, and the yield of N substituted indoles was increased by 10-15% (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…35 The structure of 1 allyl and 1 benzyl 2 methylindoles 1i,j was proved by spectral methods and confirmed by elemental analy sis data.…”

Section: Methodsmentioning

confidence: 93%

“…indoles 1a-h and 2a,b were synthesized ac cording to the described procedure, and their constants corre sponded to the literature data. 35 Synthesis of (indol 3 yl)sulfanylalkanecarboxylic acids 3a-q and 4a,b (general procedure). A solution of iodine (25.38 g, 0.1 mol) and potassium iodide (16.60 g, 0.1 mol) in 50% ethanol (50 mL) was added to a solution of indole (0.1 mol) and thiourea (15.20 g, 0.2 mol) in ethanol (50 mL) by portions in an argon flow preventing an increase in the temperature of the reaction mixture higher than 40 °С.…”

Section: Methodsmentioning

confidence: 99%

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Directed synthesis and immunoactive properties of (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)alkanecarboxylic acids

et al. 2010

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A general method for the synthesis of 1 alkyl(allyl)(benzyl) substituted (indol 3 yl) sulfanylalkanecarboxylic acids and hexane 1,6 diyl(1,4 phenylenemethylene)bisindol 3 yl sulfanylalkanecarboxylic acids from the corresponding N substituted indoles and bisindoles, thiourea, iodine, and halogencarboxylic acids was developed. The oxidation of substituted (indol 3 yl)sulfanylalkanecarboxylic acids for the first time afforded their analogs containing the sulfonyl group. New (2 hydroxyethyl)ammonium salts of 1 R indol 3 ylsulfanyl(sulfonyl) alkanecarboxylic acids, which are structural analogs of highly active immunomodulators of indacetamin and VILIM, were synthesized. Among the studied (2 hydroxyethyl)ammonium salts of 1 R indol 3 ylsulfanylacetic and sulfonylalkanecarboxylic acids, the compounds exhi biting high dose dependent antiproliferative activity by the ability to affect the spontaneous and mitogen stimulated splenocyte proliferation of mice in vitro were found.Tris(2 hydroxyethyl)ammonium salts of aroxyacetic acids, whose cation has the compact tricyclic atrane (2,8,9 trihydroprotatrane) structure favoring the penetra tion of a substance through cell membranes, are a new class of pharmacologically active substances. 1 They pos sess 2-12 anti aggregation, membrane stabilizing, antiox idant, antisclerotic, antiphlogistic, cardiotropic, analge sic, hypocholesterolemic, immunomodulating, and anti tumor activity considerably exceeding or different from the effect of the initial biologically active acids and trieth anolamine.Earlier synthesized analogs of these compounds, viz., alkanolammonium salts of (het)arylsulfanyl (sulfonyl)acetic acids (Het)ArS(SO 2 )CH 2 COO -• •N + R 1 R 2 (CH 2 CH 2 OH) n (R 1 , R 2 = H, Alk, CH 2 CH 2 OH; n = 1-3), 13-15 and their complexes with salts of biomicroelements 16,17 are lowly toxic (LD 50 = = 1300-6000 mg kg -1 ), also exhibit high and diverse bio logical activity, such as hemo and immunotropic, car diotropic, antiphlogistic, antithrombotic, antioxidant, adaptogenic, hypocholesterolemic, etc., and are highly ef ficient growth stimulating preparations for biotechnolog ical processes. 18,19 Biological activity of alkanolammonium salts of sulfur containing acids is not inferior and often exceeds the activity of related alkanolammonium salts of aroxyacetic acids. The activity is enhanced with an increase in the oxidation state of the sulfur atom and depends on the structure of the (2 hydroxyethyl)ammonium fragment. 14, 15 Indole derivatives, 20 in particular, (indol 3 yl)sulfanyl alkanecarboxylic acids and their salts, are worthy of spe cial attention as biologically active substances, 21 interme diates for the synthesis of medical preparations 22-24 and technically valuable products. 25 We have earlier found by screening efficient non toxic (LD 50 = 1300-3000 mg kg -1 ) immunoactive compounds, viz., tris(2 hydroxyethyl)ammonium indol 3 yl and 1 benzylindol 3 ylsulfanyl acetates (indacetamin and VILIM, respectively).Indacetamin has a wide range of biological activity and is an e...

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“…2 The photochemical reactions of aryl halides with thiourea afford aryl methyl sulfides, diaryl sulfides, diaryl disulfides, and arylthiols. 3 Several methodologies in the regioselective synthesis of thioethers are known; 4 however, they suffer from regiocontrol, side product formation of disulfides by self-oxidation, etc. For example, there are reports on thioether preparations utilizing thiourea, such as the reaction of pyrrole with iodine or potassium triiodide and thiourea with the formation of isothiouranium iodides, which react with halides to offer thioethers; however, this required a two-step reaction and also the involvement of additives such as hydrazine hydrates to avoid side products.…”

Section: Introductionmentioning

confidence: 99%

Thiourea-Mediated Regioselective Synthesis of Symmetrical and Unsymmetrical Diversified Thioethers

Manivel

Prabakaran

Krishnakumar

et al. 2014

Ind. Eng. Chem. Res.

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An efficient and simple thiourea-mediated regioselective synthesis of symmetrical and unsymmetrical diversified thioethers is reported. The regioselective reaction avoids byproduct formation and offers simplified methodology, wider applicability, and easy workability and an environmentally friendly approach toward symmetrical and unsymmetrical thioethers. The mechanism of formation of thiols and symmetrical and unsymmetrical thioethers involving a sulfur surrogate is described.

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Reactions of N-(Polychloroethylidene)arene-and - trifluoromethanesulfonamides with indoles

Cited by 9 publications

References 6 publications

Trifluoromethanesulfonamides and Related Compounds

Trifluoromethanesulfonamides and Related Compounds

Directed synthesis and immunoactive properties of (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)alkanecarboxylic acids

Thiourea-Mediated Regioselective Synthesis of Symmetrical and Unsymmetrical Diversified Thioethers

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