Protonation direction of 3-allylthio[1,2,4]triazino[5,6-b]indole and 3-methyl[1,3]thiazolo[3′,2′:2,3][1,2,4]triazino[5,6-b]indole

Rybakova, A. V.; Kim, D. G.; Шарутин, В. В.

doi:10.1134/s1070363214020194

Cited by 3 publications

(2 citation statements)

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“…49 Recently, much attention has been paid to the synthesis of fused triazines. 50 while the action of hydrogen halides only leads to salts 81 -products ofprotonation of the N-2 atom of the triazine moiety 52 without further electrophilic cyclization. The action of arylsulfenyl chlorides under 'doping addition' conditions (nitromethane as the solvent and LiClO 4 as the additive) regioselectively afforded the angular isomer of the fused compound 78 53 (Scheme 19).…”

Section: Short Review Synthesismentioning

confidence: 99%

“…The structures of all the mentioned products was confirmed by chemical transformations, complex spectral analyses ( 1 H, 13 C NMR, LSR NMR), and XRD studies. [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).…”

Section: Short Review Synthesismentioning

confidence: 99%

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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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