Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines
Keyword(s):
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.
2013 ◽
Vol 54
(36)
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pp. 4837-4840
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Keyword(s):
2013 ◽
Vol 78
(6)
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pp. 2430-2442
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2017 ◽
Vol 9
(12)
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pp. 10494-10503
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2013 ◽
Vol 54
(7)
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pp. 665-668
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2010 ◽
Vol 148
(1)
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pp. e28-e29
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2019 ◽
Vol 119
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pp. 376-384
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