880384-48-5Relevant academic research and scientific papers
An improved synthesis of N-Boc protected aryl amines
Darnbrough,Mervic,Condon,Burns
, p. 3273 - 3280 (2001)
There are several known methods of protecting amines as their Boc derivatives. For less nucleophilic amines such as aryl amines these methods often give poor yields and are generally not satisfactory. Here, Boc aryl amines are obtained by first introducing two Boc groups followed by selective removal of one of them. This procedure works well for a number highly sterically hindered substrates as well as electron deficient and electron rich aryl amines.
Short and simple preparation of N-Boc-protected anthranilic acid tert-butyl esters from 2-bromo-anilines
Herzig, Silvia,Kritter, Stéphane,Lübbers, Thomas,Marquardt, Nadine,Peters, Jens-Uwe,Weber, Silja
, p. 3107 - 3108 (2007/10/03)
A novel two-step procedure for the preparation of diprotected anthranilic acid derivatives from ortho-bromoanilines is described. Georg Thieme Verlag Stuttgart.
Indole synthesis by controlled carbolithiation of o-aminostyrenes
Kessler, Albane,Coleman, Claire M.,Charoenying, Patchanee,O'Shea, Donal F.
, p. 7836 - 7846 (2007/10/03)
An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.
