A short and efficient synthesis of 5,5’ -bi-1,2,3-dithiazoles

Konstantinova, Lidia S.; Bol’shakov, Oleg; Baranovsky, Ilia V.; Bogacheva, Anna M.; Strunyasheva, Vlada V.; Ракитин, Олег А.

doi:10.1016/j.mencom.2015.11.009

Cited by 12 publications

(5 citation statements)

References 15 publications

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“…While the 1,2,3-dithiazoles synthesis is well described [ 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 ], 1,2,3-thiaselenazole presented a serious synthetic challenge with relatively few methods available for construction [ 26 , 47 , 48 , 49 ]. Two literature reports assisted in our route selection to access the selected 1,2,3-thiaselenazoles [ 26 , 47 ].…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial and Antifungal Activity of Rare Substituted 1,2,3-Thiaselenazoles and Corresponding Matched Pair 1,2,3-Dithiazoles

et al. 2020

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We report our investigations into the underlying differences between 1,2,3-dithiazole and their ultra-rare counterpart, 1,2,3-thiaselenazole. This rare 1,2,3-thiaselenazole chemotype was afforded by sulfur extrusion and selenium insertion into the preconstructed 1,2,3-dithiazoles. We built a library of matched paired compounds to compare and contrast the two ring systems. This led to the development of both narrow and broad-spectrum antimicrobial compounds with sub-micro molar potency, limited to no toxicity and a further understanding of the transition state electronics through molecular simulations. We also identified the potent 4,5,6-trichlorocyclopenta[d][1,2,3]thiaselenazole 11a, for use against Candida albicans, Cryptococcus neoformans var. grubii, Staphylococcus aureus and Acinetobacter baumannii, all of which have limited clinical treatment options. The 1,2,3-thiaselenazole represents a new class of potential compounds for the treatment of a host of multi-resistant hospital derived infections.

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Section: Resultsmentioning

confidence: 99%

Antimicrobial and Antifungal Activity of Rare Substituted 1,2,3-Thiaselenazoles and Corresponding Matched Pair 1,2,3-Dithiazoles

et al. 2020

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“…IR spectra were measured with a M-80 instrument (Carl Zeiss Jena GmbH, Jena, Germany) in KBr pellets. 4,4′-Disubstituted 5,5′-bi(1,2,3-dithiazolylidenes) 11a – e [23] and ( E )-1-(4-bromophenyl)-ethan-1-one oxime [52] were prepared according to the literature.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, Rakitin et al described the Cu(0)-mediated coupling of 4-substituted 5-chloro-1,2,3-dithiazolium chlorides 10 [20,21,22] to give ( E )-4,4′-disubstituted 5,5′-bi(1,2,3-dithiazolylidenes) 11 [23]. Products 11 are similar to ( E )-3,3′-bi(1,2-dithiolylidenes) 12 that undergo both thermal and light-mediated ring transformations to afford thieno[3,2- b ]thiophenes 13 [24] (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles

et al. 2018

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Thermolysis of 4,4′-dichloro-, 4,4′-diaryl-, and 4,4′-di(thien-2-yl)-5,5′-bi(1,2,3-dithiazol-ylidenes) affords the respective 3,6-dichloro-, 3,6-diaryl- and 3,6-di(thien-2-yl)isothiazolo[5,4-d]-isothiazoles in low to high yields. The transformation of the 4,4′-diaryl- and 4,4′-di(thien-2-yl)-5,5′-bi(1,2,3-dithiazolylidenes) occurs at lower temperatures in the presence of the thiophiles triphenylphosphine or tetraethylammonium iodide. Optimized reaction conditions and a mechanistic rationale for the thiophile-mediated ring transformation are presented.

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“…Their chemistry also involves the transformation of their ring system into other systems such as pyrazolo[3,4- d ]thiazoles [ 22 ], pyridothiazoles [ 23 ], pyrido[2,3- d ]pyrimidines [ 24 ] and the rare pyrazolo[3,4- e ][ 1 , 2 , 4 ]dithiazines and benzo[ e ][ 1 , 2 , 4 ]dithiazines [ 25 ]. 1,2,3-Dithiazoles have also been used as starting materials or appeared as intermediates in various reactions [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ].…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure and Solid-State Packing of 4-Chloro-5H-1,2,3-dithiazol-5-one and 4-Chloro-5H-1,2,3-dithiazole-5-thione

et al. 2021

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The crystal structure and solid-state packing of 4-chloro-5H-1,2,3-dithiazol-5-one and two polymorphs of 4-chloro-5H-1,2,3-dithiazole-5-thione were analyzed and compared to structural data of similar systems. These five-membered S,N-rich heterocycles are planar with considerable bond localization. All three structures demonstrate tight solid-state packing without voids which is attributed to a rich network of short intermolecular electrostatic contacts. These include Sδ+…Nδ−, Sδ+…Oδ−, Sδ+…Clδ− and Sδ+…Sδ− interactions that are well within the sum of their van der Waals radii (∑VDW). B3LYP, BLYP, M06, mPW1PW, PBE and MP2 were employed to calculate their intramolecular geometrical parameters, the Fukui condensed functions to probe their reactivity, the bond order, Bird Index and NICS(1) to establish their aromaticity.

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A short and efficient synthesis of 5,5’ -bi-1,2,3-dithiazoles

Cited by 12 publications

References 15 publications

Antimicrobial and Antifungal Activity of Rare Substituted 1,2,3-Thiaselenazoles and Corresponding Matched Pair 1,2,3-Dithiazoles

Antimicrobial and Antifungal Activity of Rare Substituted 1,2,3-Thiaselenazoles and Corresponding Matched Pair 1,2,3-Dithiazoles

The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles

Crystal Structure and Solid-State Packing of 4-Chloro-5H-1,2,3-dithiazol-5-one and 4-Chloro-5H-1,2,3-dithiazole-5-thione

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