Strategies for protecting and manipulating triazine derivatives Academic Article

abstract

• Aminotriazine derivatives are available in two steps by treating chlorotriazines with acid-labile benzylic amines including triphenylmethylamine, diphenylmethylamine, and 2,4-dimethoxybenzyl-amine (Dmb-amine), followed by deprotection using trifluoroacetic acid. This high yielding (85-99%) protocol is a milder alternative to the traditional method that uses ammonia and high temperature as a route to aminotriazine derivatives. The nucleophilic substitution reaction that installs the benzylic amine on monochlorotriazine herbicide derivatives may be performed using conventional heating. Alternatively, a microwave reactor can be used to decrease the reaction times 100-fold. The intermediates in these syntheses are soluble in a range of organic solvents and amenable to chromatography. In some cases when dimethoxybenzyl groups are used, oligomerization of the dimethoxybenzyl side product upon treatment with trifluoroacetic acid yields a precipitate that facilitates purification by simple filtration. 2005 Elsevier Ltd. All rights reserved.

authors

• Bergbreiter, David

published proceedings

• TETRAHEDRON LETTERS

author list (cited authors)

• Hollink, E., Simanek, E. E., & Bergbreiter, D. E.

citation count

• 29

complete list of authors

• Hollink, E||Simanek, EE||Bergbreiter, DE

publication date

• March 2005

publisher

• Elsevier  Publisher

published in

• Tetrahedron Letters  Journal

keywords

• Protecting Group
• Triazine

Digital Object Identifier (DOI)

• 10.1016/j.tetlet.2005.01.150

start page

• 2005

end page

• 2008

volume

• 46

issue

• 12

URL

• http%3A%2F%2Fdx.doi.org%2F10.1016%2Fj.tetlet.2005.01.150