New symmetrical tetrathiafulvalene π-donors containing nine- and ten-membered dithiaheterocycles

Singh, Jai; Singh, Harkesh B.

doi:10.1039/p19920002913

Cited by 13 publications

(1 citation statement)

References 29 publications

(2 reference statements)

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“…The mechanism suggested is consistent with the fact that compounds 5 provide no cyclic products in the reaction with carbonyl compounds 2 both in acidic and basic media. The reverse recyclization of unstable 2,3-dihydropyrimidin-4(1H)-ones C to the corresponding 2,3-dihydro-1,3-thiazin-4(1H)-ones 3 proceeds via N-alkylidene derivatives D which are also likely to be intermediately form in the reaction [17], and 2-thioxo-2,3,5,6-tetrahydro-1,3-thiazin-4(1H)-ones [18]. Compounds 4 and 6 were characterized spectroscopically by the IR, 1 H NMR, and 13 C NMR methods.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2,3‐dihydro‐1,3‐thiazin‐4(1H)‐ ones and their remarkably facile recyclization to 2,3‐dihydropyrimidin‐4(1H)‐ones

Вовк

Sukach

Chernega

et al. 2005

Heteroatom Chemistry

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Functionalized 2,3‐dihydro‐1,3‐thiazin‐4(1H)‐one derivatives have been synthesized by cyclocondensation of 3‐alkyl(aryl)amino‐2‐cyano‐3‐mercaptoacrylamides with aldehydes and ketones under acidic catalysis. 6‐Alkyl(aryl)amino‐5‐cyano‐2,3‐dihy‐ dro‐1,3‐thiazin‐4(1H)‐ones, when treated with a dilute solution of potassium hydroxide, are converted into the potassium salts of isomeric compounds, 1‐alkyl‐ (aryl)‐5‐cyano‐6‐mercapto‐2,3‐dihydropyrimidin‐ 4(1H)‐ones. Alkylation of the latter with dimethyl sulfate in situ furnishes 1‐alkyl(aryl)‐6‐alkylthio‐5‐ cyano‐2,3‐dihydropyrimidin‐4(1H)‐ones, whereas boiling them in ethanol with an excess of hydrochloric acid leads to starting 2,3‐dihydro‐1,3‐thiazin‐4(1H)‐ones. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:426–436, 2005; Published online in Wiley InterScience (http://www.interscience.wiley.com). DOI 10.1002/hc.20129

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Section: Resultsmentioning

confidence: 99%

Synthesis of 2,3‐dihydro‐1,3‐thiazin‐4(1H)‐ ones and their remarkably facile recyclization to 2,3‐dihydropyrimidin‐4(1H)‐ones

Вовк

Sukach

Chernega

et al. 2005

Heteroatom Chemistry

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ChemInform Abstract: New Symmetrical Tetrathiafulvalene π Donors Containing Nine‐ and Ten‐Membered Dithiaheterocycles.

Singh

1993

ChemInform

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Thiacrown compounds: Synthesis and properties. (Review)

Литвинова¹,

Анисимов²

1999

Chem Heterocycl Compd

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Data of the last 15 vears on the synthesis and properties o/'vaiVous thiacrown compounds containing 2-8 sttlfttl" atoms in the ring are reviewed.The discovery of interesting and unique complexing charactcristics in crown ethers and their nitrogen and sulfur analogs is one of the most powcrful achievcments of modem organic chemistry. The selectivity of the macrocycle toward the ions of various mctals can be controllcd by the size of the ring, by the type, number, and position of the heteroatoms in the ring, and by the presence of functional groups in the ring and on its periphery. Of the many methods used in the synthcsis of crown ethers and their sulfur analogs (thiacrowns) the most successful is the reaction of dihalogcno dcrivatives with glycols and dithiols, by means of which it is possible to influence positively the main factors determining the selectivity of the macrocycle. Methods have been developed on the basis of this reaction for the synthesis of numerous sulfur-containing heterocyclic compounds.The various types of macrohcterocycles are of great interest as reagents that make it possible to extract metals with the object of separating thcir mixtures and subsequently determining the individual elements. Sulfurcontaining macroheterocycles and their open-chain analogs, called podands, occupy an important position in supramolocular chemistry, having the ability to connect selectively the ions of transition and heavy metals, such as Cu(II). The use of these compounds makes it possible to model the biological systems and processes in which organosulfur compounds participate. The use of macrocycles as the active components in the membranes of ionselective electrodes and molecular receptors has proved very promising.In the present review an attempt is made to summarize comprehensively the achievements of the last 10-15 years in the chemistry of thiacrown compounds containing only sulfur atoms as heteroatoms. The review is not concerned with the extensive material on the synthesis and properties of macroheterocycles containing nitrogen, oxygen, and other heteroatoms.

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New symmetrical tetrathiafulvalene π-donors containing nine- and ten-membered dithiaheterocycles

Cited by 13 publications

References 29 publications

Synthesis of 2,3‐dihydro‐1,3‐thiazin‐4(1H)‐ ones and their remarkably facile recyclization to 2,3‐dihydropyrimidin‐4(1H)‐ones

Synthesis of 2,3‐dihydro‐1,3‐thiazin‐4(1H)‐ ones and their remarkably facile recyclization to 2,3‐dihydropyrimidin‐4(1H)‐ones

ChemInform Abstract: New Symmetrical Tetrathiafulvalene π Donors Containing Nine‐ and Ten‐Membered Dithiaheterocycles.

Thiacrown compounds: Synthesis and properties. (Review)

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