Studies on quinazolines IX:1 Fluorination versus 1,2-migration in the reaction of 1,3-bifunctionalized amino-2-propanol with DAST

DOI: 10.1016/S0040-4039(98)01905-4

Source and publish data:

Tetrahedron Letters p. 8483 - 8486 (1998)

Update date:2022-09-26

Topics: Fluorination 1,2-Migration DAST

Authors:

Chern, Ji-Wang

Chang, Jun-Yi

Usifoh, Cyril O.

Gutsait, Alexander

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Article abstract of DOI:10.1016/S0040-4039(98)01905-4

Treatment of 1-phthaloylamino-3-[4-(2-methoxyphenyl)piperazin-1-yl]- propanol (7) with DAST induced 1,2-migration via a proposed spiro-aziridinium intermediate to give N-[2-fluoro-3-[4-(2-methoxyphenyl)piperazin-1- yl]propyl]-phthalimide (11a) in 13% yield and N-12-fluoromethyl-2-[4-(2- methoxyphenyl)-piperazin-1-yl]ethyl]phthalimide (11b) in 73% yield.

Full text of DOI:10.1016/S0040-4039(98)01905-4

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