A Synthetic Pathway to the 1,4-Dihydro-2H-3-benzoxocine System from Morita-Baylis-Hillman Cinnamyl Alcohols with 2,5-Dimethoxy-2,5-dihydrofuran via the Heck Reaction
- Title
- A Synthetic Pathway to the 1,4-Dihydro-2H-3-benzoxocine System from Morita-Baylis-Hillman Cinnamyl Alcohols with 2,5-Dimethoxy-2,5-dihydrofuran via the Heck Reaction
- Author
- 이기정
- Keywords
- Morita-Baylis-Hillman; Heck reaction; 1,4-dihydro-2H-3-benzoxocines; iodobenzaldehydes; 2,5-dimethoxy-2,5-dihydrofuran
- Issue Date
- 2012-12
- Publisher
- Georg Thieme Verlag KG
- Citation
- Synthesis, 2012, 44(23), P.3613-3622
- Abstract
- A new synthetic method for methyl 2-methoxy-1-(methoxycarbonylmethyl)-1,4-dihydro-2H-3-benzoxocine-5-carboxylates was developed using the Heck reaction between 2,5-dimethoxy-2,5-dihydrofuran and methyl 2-(hydroxymethyl)-3-(2-iodophenyl)propenoates as a key step. The latter were readily obtained from the Morita?Baylis?Hillman reaction of iodobenzaldehydes with methyl acrylate through acetylation, rearrangement, and hydrolysis. The methyl 2-methoxy-1-(methoxycarbonylmethyl)-1,4-dihydro-2H-3-benzoxocine-5-carboxylates were converted into methyl 2-oxo-1,2,5,11b-tetrahydro-3aH-furo[3,2-a][3]benzoxocine-6-carboxylates on exposure to excess trifluoroacetic acid.
- URI
- https://www.thieme-connect.de/DOI/DOI?10.1055/s-0032-1317471http://hdl.handle.net/20.500.11754/51175
- ISSN
- 0039-7881; 1437-210X
- DOI
- 10.1055/s-0032-1317471
- Appears in Collections:
- COLLEGE OF ENGINEERING[S](공과대학) > CHEMICAL ENGINEERING(화학공학과) > Articles
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