Tandem 'inverse electron-demand' diels-alder reactions of dienamines with a 1,2,4,5-tetrazine. A new azo-bridged ring system

András Kotschy, David M. Smith, A. Bényei

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Reaction of (EE)-1-morpholino-2-methylpenta-1,3-diene 1a with dimethyl 1,2,4,5-tetrazine-3,6-di-carboxylate 2 in acetonitrile solution gives dimethyl 2,5-dimethyl-3-morpholino-8,9-diazatricyclo[2.2,2.02,6]oct-8- ene-1,4-dicarboxylate 4a, in high yield (79%) and with high apparent diastereosolectivity; the 1-(4-methylpiperazino) analogue 1b similarly gives compound 4b (66%). Compounds 4a and 4b are the rust recorded representatives of this bridged tricyclic ring system. In contrast 2-methyl-1- morpholinocyclopentadiene 5 reacts with 2 mol. equiv. of the tetrazine 2, giving the cyclopentadipyridazine 6.

Original languageEnglish
Pages (from-to)1045-1048
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number9
DOIs
Publication statusPublished - Feb 26 1998

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Morpholinos
Cycloaddition Reaction
Electrons
1-octene
acetonitrile

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Tandem 'inverse electron-demand' diels-alder reactions of dienamines with a 1,2,4,5-tetrazine. A new azo-bridged ring system. / Kotschy, András; Smith, David M.; Bényei, A.

In: Tetrahedron Letters, Vol. 39, No. 9, 26.02.1998, p. 1045-1048.

Research output: Contribution to journalArticle

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abstract = "Reaction of (EE)-1-morpholino-2-methylpenta-1,3-diene 1a with dimethyl 1,2,4,5-tetrazine-3,6-di-carboxylate 2 in acetonitrile solution gives dimethyl 2,5-dimethyl-3-morpholino-8,9-diazatricyclo[2.2,2.02,6]oct-8- ene-1,4-dicarboxylate 4a, in high yield (79{\%}) and with high apparent diastereosolectivity; the 1-(4-methylpiperazino) analogue 1b similarly gives compound 4b (66{\%}). Compounds 4a and 4b are the rust recorded representatives of this bridged tricyclic ring system. In contrast 2-methyl-1- morpholinocyclopentadiene 5 reacts with 2 mol. equiv. of the tetrazine 2, giving the cyclopentadipyridazine 6.",
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N2 - Reaction of (EE)-1-morpholino-2-methylpenta-1,3-diene 1a with dimethyl 1,2,4,5-tetrazine-3,6-di-carboxylate 2 in acetonitrile solution gives dimethyl 2,5-dimethyl-3-morpholino-8,9-diazatricyclo[2.2,2.02,6]oct-8- ene-1,4-dicarboxylate 4a, in high yield (79%) and with high apparent diastereosolectivity; the 1-(4-methylpiperazino) analogue 1b similarly gives compound 4b (66%). Compounds 4a and 4b are the rust recorded representatives of this bridged tricyclic ring system. In contrast 2-methyl-1- morpholinocyclopentadiene 5 reacts with 2 mol. equiv. of the tetrazine 2, giving the cyclopentadipyridazine 6.

AB - Reaction of (EE)-1-morpholino-2-methylpenta-1,3-diene 1a with dimethyl 1,2,4,5-tetrazine-3,6-di-carboxylate 2 in acetonitrile solution gives dimethyl 2,5-dimethyl-3-morpholino-8,9-diazatricyclo[2.2,2.02,6]oct-8- ene-1,4-dicarboxylate 4a, in high yield (79%) and with high apparent diastereosolectivity; the 1-(4-methylpiperazino) analogue 1b similarly gives compound 4b (66%). Compounds 4a and 4b are the rust recorded representatives of this bridged tricyclic ring system. In contrast 2-methyl-1- morpholinocyclopentadiene 5 reacts with 2 mol. equiv. of the tetrazine 2, giving the cyclopentadipyridazine 6.

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