Heterocyclic Chemistry of Sulfur Chlorides – Fast Ways to Complex Heterocycles

Abstract

This microreview highlights the most important advances in the synthetic applications of sulfur dichloride and disulfur dichloride for the preparation of heterocycles. Sulfur chlorides can be considered some of the best sulfur‐transfer reagents for the synthesis of heterocyclic systems. Their high reactivity towards nucleophilic organic compounds such as alkenes, alkynes, amines, nitriles, oximes, and their both chlorinating and sulfurating character explain the extensive use of these reagents. In many cases, the initial reactions give rise to reactive intermediates that can be trapped by nucleophiles in a tandem fashion, expanding the possibilities of the reactions. In this way, several new heterocyclic systems can be obtained by a careful selection of the appropriate combination of reagents. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Switching Regioselectivity of β‐Ketothioamides by Means of Iodine Catalysis: Synthesis of Thiazolylidenes and 1,4‐Dithiines

“…In addition, polycyclic 1,4‐dithiine derivatives are useful as pigments and functional materials for electro‐optical applications 10. Although 1,4‐dithiines have been known for more than 100 years, a careful search of the literature shows that there have been no reports on the synthetic application of KTAs to construct 1,4‐dithiines 11…”

“…[10] Although 1,4-dithiines have been known for more than 100 years, a careful search of the literature shows that there have been no reports on the synthetic application of KTAs to construct 1,4-dithiines. [11] To justify that this observation was not an exception, the reactions of more KTAs with alkyl amine were investigated. The results are shown in Table 3.…”

The synthesis and characterization of solvatochromic maleimide‐fused N‐allyl‐ and N‐alkyl‐substituted 1,4‐dithiines and Diels–Alder reactions with anthracene

“…Sulfur‐containing heterocyclic compounds have held the focus of researchers along decades of historical development of organic synthesis. Their biological activities and unique structures allow several applications in different parts of pharmaceutical and agrochemical research or in material science [1].…”

“…Detailed research of 1,4‐dithiines has been limited by a lack of suitable synthetic approaches. Some 1,4‐dithiines have been known for more than 100 years, although the correct stuctures were assigned recently [1, 6, 7]. Many polycyclic 1,4‐dithiine derivatives are useful as pigments and functional materials for electrooptical applications [7].…”

One-pot synthesis of sulfur heterocycles from simple organic substrates

“…2,3 Also sulfur monochloride can be considered as a reactive electrophile 4,5 and oxidant (see examples in review [1]). But the sulfurating ability of sulfur monochloride is more important.…”