One-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis-[6-(halomethyl)- 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] and their bispyrrolocyclization

Iryna Oleksandrivna Lebedyeva, Mykhaylo V. Povstyanoy, Vyacheslav M. Povstyanoy, Oleksandr G. Panasyuk, Evgen S. Guban', Aleksey B. Ryabitskii

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A one-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis[6- (chloromethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] is proposed via three-component condensation of terephthalic aldehyde, 4-chloroacetoacetic ester, and ureas under Biginelli reaction conditions. Interaction of the obtained precursors that contain two highly reactive binucleophilic groups with primary amines leads to bis-heterocyclization with formation of (1,4-phenylene)-bis(pyrrolo[3,4-d]pyrimidine-2,5-diones).

Original languageEnglish (US)
Pages (from-to)997-1000
Number of pages4
JournalMonatshefte fur Chemie
Volume141
Issue number9
DOIs
StatePublished - Sep 1 2010
Externally publishedYes

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Aldehydes
Amines
Urea
Condensation
Esters
pyrimidine

Keywords

  • Biginelli reaction
  • Bis-heterocyclization
  • DHPM
  • Multicomponent reactions

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

One-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis-[6-(halomethyl)- 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] and their bispyrrolocyclization. / Lebedyeva, Iryna Oleksandrivna; Povstyanoy, Mykhaylo V.; Povstyanoy, Vyacheslav M.; Panasyuk, Oleksandr G.; Guban', Evgen S.; Ryabitskii, Aleksey B.

In: Monatshefte fur Chemie, Vol. 141, No. 9, 01.09.2010, p. 997-1000.

Research output: Contribution to journalArticle

Lebedyeva, Iryna Oleksandrivna ; Povstyanoy, Mykhaylo V. ; Povstyanoy, Vyacheslav M. ; Panasyuk, Oleksandr G. ; Guban', Evgen S. ; Ryabitskii, Aleksey B. / One-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis-[6-(halomethyl)- 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] and their bispyrrolocyclization. In: Monatshefte fur Chemie. 2010 ; Vol. 141, No. 9. pp. 997-1000.
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abstract = "A one-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis[6- (chloromethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] is proposed via three-component condensation of terephthalic aldehyde, 4-chloroacetoacetic ester, and ureas under Biginelli reaction conditions. Interaction of the obtained precursors that contain two highly reactive binucleophilic groups with primary amines leads to bis-heterocyclization with formation of (1,4-phenylene)-bis(pyrrolo[3,4-d]pyrimidine-2,5-diones).",
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AU - Lebedyeva, Iryna Oleksandrivna

AU - Povstyanoy, Mykhaylo V.

AU - Povstyanoy, Vyacheslav M.

AU - Panasyuk, Oleksandr G.

AU - Guban', Evgen S.

AU - Ryabitskii, Aleksey B.

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KW - Multicomponent reactions

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