期刊
JOURNAL OF COMBINATORIAL CHEMISTRY
卷 11, 期 6, 页码 1128-1135出版社
AMER CHEMICAL SOC
DOI: 10.1021/cc9001197
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资金
- National Institute of General Medical Sciences [GM070620, GM079593]
- National Institutes of Health Kansas University Chemical Methodologies and Library Development Center of Excellence [GM069663]
- Johnson Matthey, Inc
- Kawaken Fine Chemicals Co., Ltd
- Frontier Scientific and Synthonix
The solution-phase synthesis of a 167-member library of isocoumarins is described. The key intermediates for library generation, 4-iodoisocoumarins. are easily prepared by iodocyclization of the corresponding 2-(1-alkynyl)arenecarboxyl ate esters. The 4-iodoisocoumarins undergo palladium-catalyzed Sonogashira, Suzuki-Miyura, and Heck reactions to yield a diverse set of isocoumarins. Alternatively, isocoumarins, bearing hydroxyl or bromine functionalities, have been prepared by ZnCl2- and Pd(PPh3)(4)-mediated cyclization of the corresponding o-iodobenzoic acid and appropriate terminal alkynes. The resulting isocoumarins were further diversified by derivatization of the hydroxyl or bromine groups. A small set of isoquinolinones were also prepared from the corresponding isocoumarins.
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