Synthesis of thiosulfonates belonging to quinoline derivatives

S-Esters of 8-quinolinethiosulfonic acid were synthesized and tested for antimicrobial activity.     

Synthesis and applications of thiosulfonates and selenosulfonates as free-radical reagents

Chalcogenative sulfones (thiosulfonates and selenosulfonates), as reactants for organic transformations, are widely used and interesting because of their potential to react with nucleophiles, electrophiles, and free radicals. As stable radical reagents, the synthesis and applications of chalcogenative sulfones have opened up a novel pathway to synthesize many kinds of compounds containing sulfur or selenium motifs. However, despite the numerous recent works on the synthesis and applications of thiosulfonates and selenosulfonates as radical reagents, no review has yet provided a summary of the literature. In this paper, we aim to review the synthesis and applications strategies of chalcogenative sulfones as radical reagents reported over the past several decades. Different types of catalysis are discussed in this review: (i) metal catalysis; (ii) visible-light catalysis; (iii) synergistic catalysis; and (iiii) other types. Concurrently, in visible-light catalysis and metallaphotoredox catalysis sections, we highlight that developing relatively environmentally friendly synthetic methods in this area is always a great challenge, but also a persistent pursuit. Finally, the scopes, limitations, mechanisms, and existing problems of some reactions are described briefly.     

Synthesis of heterocyclic homotriptycenes

A series of novel heterocyclic homotriptycenes bearing furan, thiophene, and pyridine rings, 7a-f, were synthesized by intramolecular dehydration reactions of 10,10-dihetarylmethyl-9,10-dihydroanthracen-9-ols 6a-f. In the presence of acids, the secondary alcohols 6a-f show different reactions which depend on the electron densities of the attached heterocyclic rings. The initially formed carbenium ions react in an electrophilic substitution with electron-rich heterocycles. The formation of a transannular bridge (1,7-elimination) leads to homotriptycenes in high yields. When the heterocyclic ring has a moderate electron density, two competitive reactions exist, which afford 9-monosubstituted anthracenes by 1,4-elimination or 9,10-disubstituted anthracenes by a rearrangement, respectively. Electron-deficient heterocycles undergo a disproportionation to give hydrocarbons and ketones.     

Synthesis of heterocyclic sulfonylureas

We examined the scope of the previously reported one-pot synthesis [1] of chromone-3-sulfonylureas. Different anilines and heterocyclic amines were thereby reacted with chlorosulfonyl isocyanate-derived chlorosulfonylureas. These were treated with different enaminones and enamines to provide the title compounds.     

Synthesis of heterocyclic sulfides

2-Allylcyclopentane-1-thiol is cyclized by treatment with 75% sulfuric acid and with UV light to 2-methyl-1-thiabicyclo[3, 3, 0]octane and 1-thiabicyclo[4, 3, 0]nonane, respectively. The cyclization is stereospecific.For Part I, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1185–1187, September, 1970.     

异色满酮-4及其衍生物的合成IX异香豆素并杂环化合物的合成

本文通过3, 4-二氢异苯并吡喃酮-4和其β-二酮衍生物的缩合反应, 合成出3, 4-二氢异苯并吡喃并吲哚、并喹啉、并吡唑和并嘧啶类化合物, 并进一步氧化成标题化合物。所合成的新化合物均经核磁共振光谱红外光谱及元素分析证明其分子结构。     

Synthesis of heterocyclic phthalimidoalkyl ketones

We have investigated the 1,3-dipolar cycloaddition of dehydrobenzene, N-phenyl-maleimide, and diethyl acetylenedicarboxylate to phthalimidoalkyl diazomethyl ketones, and have obtained phthalimide derivatives of amino ketones of the indazole, pyrazole, and pyrrolo[3,4-d]-2-pyrazoline series.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 78–81, January, 1984.     

Synthesis of some heterocyclic spirocompounds

1,3-Dipolar cycloaddition reactions of methylenepyrrolidinones with nitrilimines or nitrones resulted in regio and stereoselective formation of respective spiropyrazolines or spiroisovazolidines.Department of Organic Chemistry, Slovak Technical University, Radlinského 9, 81237 Bratislava, Slovak Republic. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1353–1355, October, 1995. Original article submitted August 24, 1995.     

缩杂环卓酮化合物的合成

本文报道Friedlaender反应在卓酮化学中的应用, 合成了喹啉基取代的卓酮化合物。     

几个硫杂环配体的合成

4，5—二硫基—1，3—二硫杂戊烯—2—硫酮[dmit]的锌配合物与有机卤化物 反应，合成了含有吸电子基的1，3—二硫杂戊烯—2—硫酮的配体，用IR，^1H NMR，MS等表征了其结构．     

Thermal rearrangements of bis-allenyl thiosulfonates. Synthesis of novel thienothiophene and thieno-oxathiine derivatives

The synthesis and thermal rearrangement of bis-allenyl thiosulfonates are described. Bis-γ,γ-disubstituted allenyl thiosulfonates have been prepared by disproportionation of the corresponding allenesulfinic acids. On heating, these compounds unexpectedly rearrange to a mixture of 1H,3H-thieno[3,4-d][1,2]oxathiine-3-oxide 8, 1H,3H-thieno[3,4-c]thiophene-2,2-dioxide 9, and 3-alkyl-4-alkenylthiophene 10. A tentative reaction mechanism involving sequential sigmatropic rearrangements and cyclizations is suggested.     

Reaction of heterocyclic betaines. Synthesis of a new heterocyclic system

A new condensed heterocyclic system, viz., 1,3,7,9-tetra-oxo-2,8-diphenyl-6-formylpyrimido [3,4-a]pyrimido[4,5-dloxazine, was synthesized, and its electronic and PMR spectra were recorded. Factors that affect the orientation of nucleophilic substitution in betaines of the pyrimidine series with aliphatic amines are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 993–995, July, 1980.     

Synthesis of heterocyclic derivatives of abietane

The methods of synthesis of some new derivatives of abietane including pyridines and indoles fused with diterpene skeleton were described.     

Synthesis of new condensed heterocyclic systems

Two new diamines — [1,3-bis(5-phenyl-1,2,4-triazol-3-yl)-4,6-diamino]benzene and [1,3-di-(2-benzimldazolyl)-4,6-diamino]benzene — were synthesized from 4,6-dinitroisophthalic acid. Newheterocyclic systems — 3,5,9,11-tetraphenyl[benzo[1,2-a; 4,5-a]bis(1,2,4-triazolo[4,3-c]pyrimidine)] and 2,16-diphenyl[benzo[1,2-a;4,5-a']bis(pyrimido[1,6-a]benzimidazole)]—were obtained by reaction of the diamines with benzoyl chloride and subsequent cyclization.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1274–1277, September, 1977.     

Synthesis of heterocyclic substituted norcantharidin derivatives

Twenty novel norcantharidin derivatives, which were substituted by thiazole ring, were synthesized in a single step by the [3+2] 1,3‐dipolar cycloaddition reaction with oxime or hydrazone in the presence of chloramine‐T when compared with the conventional method. J. Heterocyclic Chem., (2011).     

Synthesis of heterocyclic bioregulators and semiochemicals

Chemistry and biology of oxygen heterocycles as insect pheromones are reviewed referring to exo-brevicomin, disparlure, japonilure and olean. Synthesis of koninginin A, a microbial metabolite, is discussed. Two azetidine alkaloids, penaresidin A and penazetidine A, were synthesized.     

Synthesis and reactions of heterocyclic compounds

5-Azido-2-methylbenzthiazole, 6-azido-1, 2-dimethyl-, and 5-azido-2-methyl-1-phenylbenzimidazoles were prepared. By the reactions of these azides with alkyl halides the quaternary slats based on the cyanine dyes were obtained.