A Novel Synthesis of Thioglycolurils by Ring Contraction of 5,7-Dialkyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones

Galina A. Gazieva; Pavel A. Poluboyarov; Leonid D. Popov; Natalya G. Kolotyrkina; Angelina N. Kravchenko; Nina N. Makhova

doi:10.1055/s-0032-1317194

Synthesis, Table of Contents

Synthesis 2012; 44(21): 3366-3370
DOI: 10.1055/s-0032-1317194

paper

A Novel Synthesis of Thioglycolurils by Ring Contraction of 5,7-Dialkyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones

Galina A. Gazieva*

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Fax: +7(499)1355328 Email: gaz@ioc.ac.ru

,

Pavel A. Poluboyarov

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Fax: +7(499)1355328 Email: gaz@ioc.ac.ru

,

Leonid D. Popov

^bDepartment of Chemistry, Southern Federal University, 7 Zorge Street, 344090 Rostov-on-Don, Russian Federation

,

Natalya G. Kolotyrkina

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Fax: +7(499)1355328 Email: gaz@ioc.ac.ru

,

Angelina N. Kravchenko

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Fax: +7(499)1355328 Email: gaz@ioc.ac.ru

,

Nina N. Makhova

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Fax: +7(499)1355328 Email: gaz@ioc.ac.ru

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Abstract

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Abstract

A new synthetic route to (E)-1,3-dialkyl-4-(benzylideneamino)-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-ones (thioglycolurils), by a ring contraction reaction of 5,7-dialkyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones with aromatic aldehydes, has been developed.

Key words

N-heterocycles - thioglycolurils - 3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones - aromatic aldehydes - ring contraction

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References

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