Synthesis of α,ω-bis-1,5,3-dithiazepanes and their fungicidal properties

Rakhimova, E. B.; Исмагилов, Р. Р.; Zainullin, R. A.; Galimzyanova, N. F.; Ибрагимов, А. Г.

doi:10.1134/s1070427213100066

Cited by 13 publications

(5 citation statements)

References 8 publications

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“…As a continuation of the research into catalytic synthesis of heterocyclic compounds [36][37][38][39][40][41][42][43][44] and to develop a selective route to 42-…”

Section: Resultsmentioning

confidence: 99%

Samarium(III) nitrate-catalyzed one-pot synthesis of 42-membered N,S,O-containing cyclophanes

Makhmudiyarova¹,

Khatmullina²,

Mescheryakova³

et al. 2016

Arkivoc

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“…As a continuation of the research into catalytic synthesis of heterocyclic compounds [36][37][38][39][40][41][42][43][44] and to develop a selective route to 42-…”

Section: Resultsmentioning

confidence: 99%

Samarium(III) nitrate-catalyzed one-pot synthesis of 42-membered N,S,O-containing cyclophanes

Makhmudiyarova¹,

Khatmullina²,

Mescheryakova³

et al. 2016

Arkivoc

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“…[14][15][16][17][18][19][20][21][22] The structure of some compounds was unequivocally determined with the use of an X-ray tech-nique. [14][15][16][17][18][19][20][21][22] The structure of some compounds was unequivocally determined with the use of an X-ray tech-nique.…”

Section: Introductionmentioning

confidence: 99%

“…Cyclic sulphur-and nitrogen-containing compounds were successfully synthesized via multicomponent reactions (MCRs) between amino substrates, formaldehyde, and SH acids in recent years. [14][15][16][17][18][19][20][21][22] The structure of some compounds was unequivocally determined with the use of an X-ray tech-nique. Moreover, the stereoelectronic effects and interactions in N-C-S, N-N-C, and lp-S-C-NH + systems of the related compounds were revealed.…”

Section: Introductionmentioning

confidence: 99%

Intermolecular interactions and chiral crystallization effects in (1,5,3-dithiazepan-3-yl)-alkanoic acids

et al. 2016

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Crystals of (1,5,3-dithiazepan-3-yl)-alkanoic acids with achiral and chiral amino acid moieties have been obtained, and their structures were studied using a single crystal X-ray technique. Simple crystal systems, namely monoclinic, triclinic, and orthorhombic, were revealed in a series of the studied compounds. The reference 1,5,3-dithiazepan-3-ol forms head-to-head cyclic dimeric associates R 2 2 (6) via strong O-H⋯N intermolecular hydrogen bonds. The achiral 1,5,3-dithiazepanes form head-to-head cyclic dimers R 2 2 (8) between two carboxylic groups, whereas the co-crystals involve solvent molecules to constitute dimeric pairs R 3 3 (11) and R 2 2 (8) through O⋯H and N⋯H hydrogen bonds. These dimers further contribute to the aggregation of layers and stacks due to diverse H⋯H and S⋯H contacts. The chiral dithiazepanes form head-totail R 1 2 (6), R 2 2 (7), and R 2 2 (8) cyclic dimers between the carboxylic group of one molecule and the dithiazepane moiety of the other one through H⋯H, S⋯H, and O⋯H intermolecular contacts. Hirshfeld analysis has shown that S⋯H (9.2-19.8%) and O⋯H (5.4-18.2%) intermolecular hydrogen bonds as well as weak H⋯H contacts (40.2-64.0%) are predominant in all the compounds to form crystal packing. CrystEngCommThis journal is † Electronic supplementary information (ESI) available: Additional tables with some bonds and with crystal data and structure refinement of the studied compounds. Fig. 12 Fragments of the crystal packing of 7 with intermolecular contacts. View along the b axis.Fig. 13 Fragments of crystal packing of 8: (a and b) view along the c axis and (c) along the b axis. CrystEngCommPaper

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“…There are no literature references regarding the preparation of N-hydroxyalkyl-1,5,3-dithiazepanes. The interest in this class of heterocycles is motivated by their possible use as fungicides [5,6].In order to develop an effective catalytic method for the synthesis of N-hydroxyalkyl-1,5,3-dithiazepanes, we studied the recyclization of 1-oxa-3,6-dithiacycloheptane (1) with amino alcohols. The preliminary experiments indicated that the uncatalyzed interaction of 2-amino-2-methylpropane-1,3-diol with equimolar quantity of 1-oxa-3,6-dithiacycloheptane (1) in an EtOH-CHCl 3 solvent mixture at room temperature over 3 h led to the formation of 2-(1,5,3-dithiazepan-3-yl)-2-methylpropane-1,3-diol (2) in a yield not exceeding 20%.…”

mentioning

confidence: 99%

mentioning

confidence: 99%

Synthesis of N-Hydroxyalkyl-1,5,3-Dithiazepanes Based on Amino Alcohols

Rakhimova

Исмагилов

Mescheryakova

et al. 2014

Chem Heterocycl Comp

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Catalytic methods were developed for the synthesis of N-hydroxyalkyl-1,5,3-dithiazepanes by recyclization of 1-oxa-3,6-dithiacycloheptane with amino alcohols and by intermolecular cyclization of 1,2-ethanedithiol with methoxymethylamino alcohols.According to published data [1], one of the methods for the synthesis of N-substituted 1,5,3-dithiazepanes is the three-component condensation of primary amines with formaldehyde and 1,2-ethanedithiol. Another method is based on the catalytic recyclization of 1,3,5-triazin-2-one with 1,2-ethanedithiol [2] or 1-oxa-3,6-dithiacycloheptane with primary amines, as well as using the transamination of N-alkyl-1,5,3-di-thiazepanes with aniline derivatives [3] or aliphatic ,ω-diamines [4]. There are no literature references regarding the preparation of N-hydroxyalkyl-1,5,3-dithiazepanes. The interest in this class of heterocycles is motivated by their possible use as fungicides [5,6].In order to develop an effective catalytic method for the synthesis of N-hydroxyalkyl-1,5,3-dithiazepanes, we studied the recyclization of 1-oxa-3,6-dithiacycloheptane (1) with amino alcohols. The preliminary experiments indicated that the uncatalyzed interaction of 2-amino-2-methylpropane-1,3-diol with equimolar quantity of 1-oxa-3,6-dithiacycloheptane (1) in an EtOH-CHCl 3 solvent mixture at room temperature over 3 h led to the formation of 2-(1,5,3-dithiazepan-3-yl)-2-methylpropane-1,3-diol (2) in a yield not exceeding 20%. For the purpose of optimizing the yield of the heterocycle 2, recyclization of 1-oxa-3,6-dithiacycloheptane (1) with amino alcohol was performed in the presence of catalysts based on salts of transition metals (Cu, Pd, Co, Ni, Zr, Ti) and rare earth metals (Eu, Er, Yb, La, Sm), which have shown high activity in heterocyclization reactions [7,8]. The highest activity in this reaction was observed for the catalysts based on rare earth metal salts, where the yield of 2-(1,5,3-dithiazepan-3-yl)-2-methylpropane-1,3-diol (2) increased in the following order (5 mol% of catalysts were used): EuCl 3 ·6H 2 O (45%), Er(NO 3 ) 3 ·6H 2 O (49%),

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Synthesis of α,ω-bis-1,5,3-dithiazepanes and their fungicidal properties

Cited by 13 publications

References 8 publications

Samarium(III) nitrate-catalyzed one-pot synthesis of 42-membered N,S,O-containing cyclophanes

Samarium(III) nitrate-catalyzed one-pot synthesis of 42-membered N,S,O-containing cyclophanes

Intermolecular interactions and chiral crystallization effects in (1,5,3-dithiazepan-3-yl)-alkanoic acids

Synthesis of N-Hydroxyalkyl-1,5,3-Dithiazepanes Based on Amino Alcohols

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