The application of the Diels-Alder reaction in the synthesis of some nitrogen heterocycles
The application of the Diels-Alder reaction in the synthesis of some nitrogen heterocycles
A review of the intramolecular Diels-Alder reaction is given and the intention of investigating the cycloaddition of a number of amido trienes introduced. Six acyclic, secondary amino dienes were synthesised from sorbic acid and from penta-2(E),4-dienoic acid. These dienes were treated with acryloyl chloride to yield trienes which were thermally cyclised to give, in each case, a mixture of cis- and trans-fused lactams. A number of highly functionalised 8-azabicyclo[4.3.0]non-2-en-7-ones were obtained from the intramolecular Diels-Alder reaction of the trienes generated in situ from the amino dienes and dichloromaleic-, bromomaleic- and maleic-anhydride. All the trienes cyclised with a high level of anti selectivity. Aspects of the chemistry of these functionalised lactams were investigated. Dechlorodecarboxylation, dehydrohalogenation, dehalogenation and hydrogenation reactions yielded a number of interesting bicyclic lactams. The dechlorodecarboxylation reaction was studied in some detail. It was found that depending on the substitution of the substrate, conjugated or non-conjugated products were produced. The imino Diels-Alder reaction is reviewed. A model study was made of the Diels-Alder reactions between 4,9-dihydro-3H-pyrido [3,4-b] indole and the dienes methyl-penta-2(E),4-dienoate, 1-cyano-buta-1(E),3-diene and 1-methoxy-3-trimethylsilyloxy-buta-1(E),3-diene. A new method for the synthesis of 1-cyano-buta-1(E),3-diene was developed. An attempt to develop this chemistry, by studying the cycloaddition of the tryptophan derived imine methyl-4,9-dihydro-3H-pyrido[3,4-b]-indole-3-carboxylate with a number of dienes under various conditions was unsuccessful. (D80018)
University of Southampton
1987
Wagland, Alison Mary
(1987)
The application of the Diels-Alder reaction in the synthesis of some nitrogen heterocycles.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
A review of the intramolecular Diels-Alder reaction is given and the intention of investigating the cycloaddition of a number of amido trienes introduced. Six acyclic, secondary amino dienes were synthesised from sorbic acid and from penta-2(E),4-dienoic acid. These dienes were treated with acryloyl chloride to yield trienes which were thermally cyclised to give, in each case, a mixture of cis- and trans-fused lactams. A number of highly functionalised 8-azabicyclo[4.3.0]non-2-en-7-ones were obtained from the intramolecular Diels-Alder reaction of the trienes generated in situ from the amino dienes and dichloromaleic-, bromomaleic- and maleic-anhydride. All the trienes cyclised with a high level of anti selectivity. Aspects of the chemistry of these functionalised lactams were investigated. Dechlorodecarboxylation, dehydrohalogenation, dehalogenation and hydrogenation reactions yielded a number of interesting bicyclic lactams. The dechlorodecarboxylation reaction was studied in some detail. It was found that depending on the substitution of the substrate, conjugated or non-conjugated products were produced. The imino Diels-Alder reaction is reviewed. A model study was made of the Diels-Alder reactions between 4,9-dihydro-3H-pyrido [3,4-b] indole and the dienes methyl-penta-2(E),4-dienoate, 1-cyano-buta-1(E),3-diene and 1-methoxy-3-trimethylsilyloxy-buta-1(E),3-diene. A new method for the synthesis of 1-cyano-buta-1(E),3-diene was developed. An attempt to develop this chemistry, by studying the cycloaddition of the tryptophan derived imine methyl-4,9-dihydro-3H-pyrido[3,4-b]-indole-3-carboxylate with a number of dienes under various conditions was unsuccessful. (D80018)
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Published date: 1987
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Local EPrints ID: 461391
URI: http://eprints.soton.ac.uk/id/eprint/461391
PURE UUID: 61b5bb36-7b95-4de6-ac65-884178150b5e
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Date deposited: 04 Jul 2022 18:45
Last modified: 04 Jul 2022 18:45
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Author:
Alison Mary Wagland
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