2026-09-20T19:42:09Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/460342022-01-13T07:54:21Zcom_1721.1_7582com_1721.1_7581col_1721.1_131022
Rick L. Danheiser.
Mak, Xiao Yin
Massachusetts Institute of Technology. Dept. of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2009-06-30T17:06:15Z
2009-06-30T17:06:15Z
2008
2008
http://hdl.handle.net/1721.1/46034
367601332
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.
Vita.
Includes bibliographical references.
A tandem benzannulation-ring closing metathesis strategy for the efficient synthesis of benzo-fused nitrogen heterocycles such as dihydroquinolines, benzazepines, and benzazocines has been developed. This strategy is based on the benzannulation reaction of ynamides with cyclobutenones or [alpha]-diazo ketones to generate highly-substituted aniline derivatives, which then participate in ring-closing metathesis reactions to form nitrogen heterocycles. The synthetic utility of this strategy has been demonstrated by its successful application in a formal synthesis of the natural product (+)-FR900482. In addition, an environmentally-friendly approach to the synthesis of amides and lactams has been developed using supercritical carbon dioxide as a 'green' replacement solvent. The amide products are generated from the addition of amines to ketenes, which are formed in situ from the retro-ene reaction of alkynyl ethers.
by Xiao Yin Mak.
Ph.D.
2 v. (311 leaves)
eng
Massachusetts Institute of Technology
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http://dspace.mit.edu/handle/1721.1/7582
Chemistry.
Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ;
Formal synthesis of (+)-FR900482
Thesis
application/pdf
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<Abstract>A tandem benzannulation-ring closing metathesis strategy for the efficient synthesis of benzo-fused nitrogen heterocycles such as dihydroquinolines, benzazepines, and benzazocines has been developed. This strategy is based on the benzannulation reaction of ynamides with cyclobutenones or [alpha]-diazo ketones to generate highly-substituted aniline derivatives, which then participate in ring-closing metathesis reactions to form nitrogen heterocycles. The synthetic utility of this strategy has been demonstrated by its successful application in a formal synthesis of the natural product (+)-FR900482. In addition, an environmentally-friendly approach to the synthesis of amides and lactams has been developed using supercritical carbon dioxide as a 'green' replacement solvent. The amide products are generated from the addition of amines to ketenes, which are formed in situ from the retro-ene reaction of alkynyl ethers.</Abstract>
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