Sulfonamide Analogues of Creatinine. The Synthesis of 3-Amino-4,5-dihydro-1,2,4-thiadiazole 1,1-Dioxides from Base-Induced Cyclization Reactions

Fares A. Fares; Damon D. Ridley; Ping Yin

doi:10.1071/c97159

Sulfonamide Analogues of Creatinine. The Synthesis of 3-Amino-4,5-dihydro-1,2,4-thiadiazole 1,1-Dioxides from Base-Induced Cyclization Reactions

Australian Journal of Chemistry ◽

10.1071/c97159 ◽

1997 ◽

Vol 50 (10) ◽

pp. 1027 ◽

Cited By ~ 6

Author(s):

Fares A. Fares ◽

Damon D. Ridley ◽

Ping Yin

Keyword(s):

Methyl Iodide ◽

Cyclization Reactions ◽

Methyl Derivative

We report the preparation of 3-amino-4,5-dihydro-1,2,4-thiadiazole 1,1-dioxide and of its 4-methyl derivative which are of interest as potential analogues of creatinine. The thiadiazoles are obtained from chloromethylsulfonylation ofS-benzylisothiourea, followed by cyclization of the chloromethanesulfonamide under basic conditions in the presence of 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile or of methyl iodide.

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Potential antihistamine agents: 4-(6,11-Dihydrodibenzo[b,e]thiepin-11-ylidene)-1-methyltetrahydrothiopyranium iodide and similar sulfonium salts derived from related tricyclic systems

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19872758 ◽

1987 ◽

Vol 52 (11) ◽

pp. 2758-2774 ◽

Cited By ~ 4

Author(s):

Zdeněk Polívka ◽

Jiří Holubek ◽

Miloš Buděšínský ◽

Oluše Matoušová ◽

Emil Svátek ◽

...

Keyword(s):

Methyl Iodide ◽

Methyl Derivative ◽

Sulfonium Salt ◽

Sulfonium Salts ◽

Central Effects ◽

Tertiary Alcohols ◽

Antihistamine Activity ◽

Grignard Reactions ◽

By Products

Thioxanthone, 10,11-dihydrodibenzo[a,d]cyclohepten-5-one, dibenzo[b,e]thiepin-11(6H)-one, its 2-methyl derivative, and thieno[2,3-c]-2-benzothiepin-4(9H)-one were reacted with 4-tetrahydrothiopyranylmagnesium bromide and the obtained tertiary alcohols IVabc, VIc, and XIX were dehydrated to the olefinic sulfides IXabc, Xc, and XXI. Addition of methyl iodide afforded the title compounds XIabc, XIIc, and XXII. The Grignard reactions were accompanied by the 1,6-addition giving the ketones XVI-XVIII as by-products. The reductive properties of tetrahydrothiopyranylmagnesium bromide were most striking in the case of reaction with 2-chlorothioxanthone; the isolation of thioxanthene and thioxanthone showed that nuclear dehalogenation took also place. Reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin and benzhydryl chloride with tetrahydrothiopyran-4-ol gave the sulfides XXV and XXVIII; whereas the latter reacted with methyl iodide under the formation of sulfonium salt XXIX, the former was cleaved and gave 4-hydroxyl-1-methyltetrahydrothiopyranium iodide (XXVI). The sulfonium salts are free of the central effects but their antihistamine activity is rather low.

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Cyclization of Ph2Si(NHNHMe)2. II. Reactions with methyl iodide, HCl, and Ph2SiCl2, and thermolysis

Canadian Journal of Chemistry ◽

10.1139/v94-222 ◽

1994 ◽

Vol 72 (8) ◽

pp. 1759-1763 ◽

Cited By ~ 4

Author(s):

Jiliang He ◽

John F. Harrod

Keyword(s):

Methyl Iodide ◽

Membered Ring ◽

Cyclization Reactions

The reaction of Ph2Si(NHNHMe)2 (1) with MeI results in a mixture of two six-membered ring isomers, 1,2,4,5-tetraaza-1,4-dimethyl-3,3,6,6-tetraphenyl-3,6-disilacyclohexane (2), 45%, and 1,2,4,5-tetraaza-1,5-dimethyl-3,3,6,6-tetraphenyl-3,6-disilacyclohexane (3), 40%. The reaction of 1 with HCl or Ph2SiCl2 proceeds in a similar fashion. The thermolysis of 1 is studied from 25–600 °C. In the range of 250–300 °C, about 50% of 1 is converted into 2,3, and 1,2,4-triaza-1-methyl-4-methylamino-3,3,5,5-tetraphenyl-3,5-disilacyclopentane, 8. Possible pathways for the formation of 2,3, and 8 in these cyclization reactions are discussed.

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Syntheses of 1, 2, and 9-methyl derivatives of 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and their antiviral activity

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19851057 ◽

1985 ◽

Vol 50 (5) ◽

pp. 1057-1063 ◽

Cited By ~ 13

Author(s):

Stanislav Rádl ◽

Viktor Zikán ◽

František Šmejkal

Keyword(s):

Influenza Virus ◽

Antiviral Activity ◽

Methyl Iodide ◽

Room Temperature ◽

Encephalomyocarditis Virus ◽

Methyl Derivative ◽

Sodium Salts ◽

Methyl Derivatives ◽

Derivatives Of

The paper describes syntheses of 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline (Ia), its 1-methyl derivative (Ib), 2-methyl derivative (IIa), 9-methyl derivative (Ic), 1,9-dimethyl derivative (Id) and 2,9-dimethyl derivative (IIb). Sodium salts of compounds Ia, Ib, Ic and IIa were methylated with methyl iodide in dimethylformamide at room temperature, compounds Id and IIb were demethylated with pyridine hydrochloride. The compounds prepared were tested for antiviral activity in vivo in mice against influenza virus A2-Hongkong and the Encephalomyocarditis virus.

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Metal-Catalyzed Cyclization Reactions 1

10.1055/b-003-129294 ◽

2016 ◽

Cited By ~ 1

Keyword(s):

Cyclization Reactions ◽

Metal Catalyzed

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Metal-Catalyzed Cyclization Reactions 2

10.1055/b-004-129734 ◽

2016 ◽

Keyword(s):

Cyclization Reactions ◽

Metal Catalyzed

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Mechanistic Study and Development of Catalytic Reactions of Sm(II)

10.26434/chemrxiv.7355069 ◽

2018 ◽

Author(s):

Sandepan Maity ◽

Robert Flowers

Keyword(s):

Molecular Weight ◽

High Molecular Weight ◽

Proton Donor ◽

Catalytic Reactions ◽

Mechanistic Study ◽

Mechanistic Studies ◽

Cyclization Reactions ◽

Mechanistic Approach ◽

Donor Source

Despite the broad utility and application of SmI2in synthesis, the reagent is used in stoichiometric amounts and has a high molecular weight, resulting in a large amount of material being used for reactions requiring one or more equivalents of electrons. We report mechanistic studies on catalytic reactions of Sm(II) employing a terminal magnesium reductant and trimethyl silyl chloride in concert with a non-coordinating proton donor source. Reactions using this approach permitted reductions with as little as 1 mol% Sm. The mechanistic approach enabled catalysis employing HMPA as a ligand, facilitating the development of catalytic Sm(II) 5-exo-trig ketyl olefin cyclization reactions.

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Substance Overview for Methyl iodide

The MAK-Collection for Occupational Health and Safety ◽

10.1002/3527600418.mbe7488 ◽

2014 ◽

pp. 1-1

Keyword(s):

Methyl Iodide

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Automated C-11 Methyl Iodide/Triflate Production: Current State of the Art

Current Organic Chemistry ◽

10.2174/13852728113179990104 ◽

2013 ◽

Vol 17 (19) ◽

pp. 2119-2126 ◽

Cited By ~ 1

Author(s):

Bruce Mock

Keyword(s):

Methyl Iodide ◽

State Of The Art ◽

Current State

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6,11-Dihydrodibenzo[b,e]thiepin-11-yl 3-quinuclidinyl ethers: New potential intidepressants and antihistamine agents

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19881806 ◽

1988 ◽

Vol 53 (8) ◽

pp. 1806-1811 ◽

Cited By ~ 2

Author(s):

Zdeněk Polívka ◽

Jan Metyš ◽

Miroslav Protiva

Keyword(s):

Methyl Derivative ◽

Antihistamine Activity ◽

Antidepressant Agent ◽

Anticataleptic Activity

Reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin and its 2-methyl derivative, and further of the methanesulfonates of 2-chloro- and 2-bromo-6,11-dihydrodibenzo[b,e]thiepin-11-ol with 3-quinuclidinol afforded the title ethers I-IV. The 2-methyl compound II (VÚFB-17 088) showed significant antihistamine activity and the 2-chloro compound III (VÚFB-17 089), having antireserpine and anticataleptic activity, proved a potential antidepressant agent.

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