The intramolecular cyclization of 31 polyhalogen-substituted pyridines containing N,N-dialkyldithiocarbamate or alkylxanthate groups has been compared as a reaction in solution with sodium N,N-dialkyldithiocarbamates or potassium carbethoxydithiolate and as a gas-phase reaction under electron ionization (EI) conditions. A scheme of fragmentation for the studied compounds has been proposed. The influence of the nature of leaving groups (Cl, F, CF 3 , CN, COOEt), of the presence of electron-withdrawing groups (Cl, F, CN, CCl 3 , CF 3 , COOEt) that are ortho, meta or para to the leaving halogen, of the position of a dithio group with respect to the pyridine nitrogen atom and of the role of oxygen and nitrogen in the corresponding alkylxanthates and N,N-dialkyldithiocarbamates on the cyclization process has been investigated.

Nitrogen atom

Leaving group

10.1255/ejms.595

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Mass-spectrometric study of the cyclization of diazo ketones. 6. Cyclization of 1-diazo-3-aroylaminopropan-2-ones and 2-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ones

Chemistry of Heterocyclic Compounds (1983)

Аlbert T. Lebedev P. A. Sharbatyan A. M. Sipyagin В. Г. Карцев Valery S. Petrosyan

Wolff rearrangement

10.1007/bf00505752

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Reactions of Polyhalopyridines. 17. Synthesis of 2-, 3-, and 4-Perfluoroalkylthiopolychloropyridines

Chemistry of Heterocyclic Compounds (2003)

A. M. Sipyagin V. S. Enshov G. N. Boǐko Аlbert T. Lebedev N. K. Karakhanova

Thiol

Chlorine atom

Fluorine

Nitrogen atom

10.1023/b:cohc.0000014415.38746.ee

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Citations (4)

New method for the synthesis of the 1,3-thiazine system. 2-phenylamino-5,6-dihydro-4H-1,3-thiazin-5-ones

Chemistry of Heterocyclic Compounds (1980)

В. Г. Карцев A. M. Sipyagin Nikolai F. Sepetov L A Sibel'dina

Thiazine

10.1007/bf00496597

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ChemInform Abstract: MASS‐SPECTROMETRIC STUDY OF THE CYCLIZATION OF DIAZO KETONES. 3. CYCLIZATION OF O‐(BENZENESULFONAMIDO)‐Ω‐DIAZOACETOPHENONES TO N‐(BENZENESULFONYL)INDOXYLS

Chemischer Informationsdienst (1983)

Аlbert T. Lebedev P. A. Sharbatyan A. M. Sipyagin В. Г. Карцев V.S. Petrosyan

10.1002/chin.198305065

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ChemInform Abstract: Reactions of Polyhalopyridines. Part 7. New Synthesis of Carbonyl- Containing Derivatives of Polychloro-2-thiopyridines.

ChemInform (1995)

A. M. Sipyagin V. V. Kolchanov N. N. Sveshnikov

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

10.1002/chin.199510164

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