Direct synthesis of phosphonates and α-amino-phosphonates from 1,3-benzoxazines
A straightforward and novel method for transformation of readily available 1,3-benzoxazines to secondary phosphonates and α-aminophosphonates using boron trifluoride etherate as catalyst is developed. The formation of phosphonates proceeds through ortho-quinone methide (o-QM) generated in situ, followed by a phospha-Michael addition reaction. On the other hand, the α-aminophosphonates were obtained by iminium ion formation and the subsequence nucleophilic substitution of alkylphosphites. This method can be also used for the preparation of o-hydroxybenzyl ethers through oxa-Michael addition.
Studies on the Benzoxazine Series. Part 3 - Preparation and 13C NMR Structural Study of γ Effects of Some N-Subsitituted 3,4-Dihydro-2H-1,3-benzoxazines
Seventeen N-substituted 3,4-dihydro-2H-1,3-benzoxazines i, But, CH2C6H5 or CH(CH3)C6H5> were prepared and their structures studied in the light of 13C chemical shifts.The γ effects caused by C(α)-methyl or C(α)
Neuvonen, Kari,Pihlaja, Kalevi
p. 239 - 245
(2007/10/02)
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