Synthesis of novel [1,3]thiazino[3´,2´:2,3][1,2,4]triazino[5,6-b]indole derivatives

Rybakova, A. V.; Kim, D. G.; Ежикова, М. А.; Кодесс, М. И.; Taherc, I. A. T.

doi:10.1007/s11172-015-0952-0

Cited by 4 publications

(1 citation statement)

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“…[50][51][52][53][54] The same group later reported the effect of a substituent on the double bond on the regioselectivity of the ring closure. Thus, the halogenation of terminally disubstituted propenyl and 3-butenyl thioethers 83 and 84 gives 55 However the halogenation of 3-chloropropenyl and 2substituted propenyl thioethers 86 and 87 demonstrated a facile access to the product of thiazole ring annulation (Scheme21). 56 It was also reported that propargyl thioether 89 gave Z- 6-b]indolium salt 90 stereoselectively under the action of bromine in acetic acid with ice cooling, or in the presence of iodine in chloroform at room temperature (Scheme 22).…”

Section: Short Review Synthesismentioning

confidence: 99%

The Use of Electrophilic Cyclization for the Preparation of Condensed Heterocycles

Slivka¹,

Onysko²

2021

Synthesis

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Condensed heterocycles are well-known for their excellent biological effects and they are undeniably important compounds in organic chemistry. Electrophilic cyclization reactions are widely used for the synthesis of mono-heterocyclic compounds. This review highlights the utility of electrophilic cyclization reactions as an effective generic tool for the synthesis of various condensed heterocycles containing functional groups that are able to undergo further chemical transformations, such as nucleophilic substitution, elimination, re-cyclization, cleavage, etc. This review describes the reactions of unsaturated derivatives of different heterocycles with various electrophilic agents (halogens, arylsulfanyl chlorides, mineral acids) resulting in annulation of an additional partially saturated heterocycle. The electrophilic reaction conditions, plausible mechanisms and the use of such transformations in organic synthesis are also discussed. The review mainly focuses on research published since 2002 in order to establish the current state of the art in this area. 1 Introduction2 Electrophilic Cyclization Pathways Involving a Nitrogen Nucleophilic Center3 Electrophilic Cyclization Pathways Involving a Chalcogen Nucleophilic Center3.1 Sulfur Centers3.2 Oxygen Centers3.3 Selenium Centers4 Strategies and Mechanisms5 Conclusion

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