Synthesis of 2-Silatetralin Derivatives Bearing Oxygen Functional Groups
摘要:
The Grignard reagents of methoxy- or methylene-dioxyphenylmethyl chlorides (12a-e) were treated with trichloro-vinylsilane in THF or ether to give methoxy- or methylenedioxy-benzyldichlorovinylsilanes (13a-e). The reaction of 13a-d in the presence of AlCl3 in CS2 or CH2Cl2 followed by treatment with MeOH and cyclohexylamine or Et3N afforded methoxy-2-silatetralins (16a-d). Treatment of 16a-d with MeMgl or EtMgBr in ether gave the corresponding 2,2-dimethyl- or 2,2-diethyl-2-silatetralins (17a-d or 18). Demethylation of 17a, 17b or 18 with BBr3 in CH2Cl2 furnished hydroxy-2-silatetralins (19a, 19b or 20).
Synthesis of 2-Silatetralin Derivatives Bearing Oxygen Functional Groups
摘要:
The Grignard reagents of methoxy- or methylene-dioxyphenylmethyl chlorides (12a-e) were treated with trichloro-vinylsilane in THF or ether to give methoxy- or methylenedioxy-benzyldichlorovinylsilanes (13a-e). The reaction of 13a-d in the presence of AlCl3 in CS2 or CH2Cl2 followed by treatment with MeOH and cyclohexylamine or Et3N afforded methoxy-2-silatetralins (16a-d). Treatment of 16a-d with MeMgl or EtMgBr in ether gave the corresponding 2,2-dimethyl- or 2,2-diethyl-2-silatetralins (17a-d or 18). Demethylation of 17a, 17b or 18 with BBr3 in CH2Cl2 furnished hydroxy-2-silatetralins (19a, 19b or 20).