Preparation of 9-amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-dione by a retro-Diels-Alder reaction

G. Stájer, Ferenc Miklós, P. Sohár, Reijo Sillanpää

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Treatment of di-endo- or di-exo-3-aminobicyclo[2.2.1]hept-5-ene-2-carbohydrazides (1a and 1b) with ethyl 2-(2-oxocyclopentyl)acetate (2) yields norbornene-condensed 9-amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-diones 3a and 3b, the condensed bis(lactams) 4a and 4b and (from 1b and 2) the cyclopenta[c]pyridazinone 5. After separation, 3a and 3b both decompose on heating by loss of cyclopentadiene to give 9-amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-dione (6).

Original languageEnglish
Pages (from-to)4153-4156
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number21
Publication statusPublished - Nov 2001

Fingerprint

Cycloaddition Reaction
Cyclopentanes
Lactams
Heating
Acetates
n-dodecane
2-norbornene
carbohydrazide

Keywords

  • Cycloreversions
  • Nitrogen heterocycles
  • Polycycles
  • Retro reactions

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Preparation of 9-amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-dione by a retro-Diels-Alder reaction. / Stájer, G.; Miklós, Ferenc; Sohár, P.; Sillanpää, Reijo.

In: European Journal of Organic Chemistry, No. 21, 11.2001, p. 4153-4156.

Research output: Contribution to journalArticle

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AU - Miklós, Ferenc

AU - Sohár, P.

AU - Sillanpää, Reijo

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N2 - Treatment of di-endo- or di-exo-3-aminobicyclo[2.2.1]hept-5-ene-2-carbohydrazides (1a and 1b) with ethyl 2-(2-oxocyclopentyl)acetate (2) yields norbornene-condensed 9-amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-diones 3a and 3b, the condensed bis(lactams) 4a and 4b and (from 1b and 2) the cyclopenta[c]pyridazinone 5. After separation, 3a and 3b both decompose on heating by loss of cyclopentadiene to give 9-amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-dione (6).

AB - Treatment of di-endo- or di-exo-3-aminobicyclo[2.2.1]hept-5-ene-2-carbohydrazides (1a and 1b) with ethyl 2-(2-oxocyclopentyl)acetate (2) yields norbornene-condensed 9-amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-diones 3a and 3b, the condensed bis(lactams) 4a and 4b and (from 1b and 2) the cyclopenta[c]pyridazinone 5. After separation, 3a and 3b both decompose on heating by loss of cyclopentadiene to give 9-amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-dione (6).

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KW - Polycycles

KW - Retro reactions

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