16697-83-9Relevant articles and documents
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Chaplin,Hunter
, p. 1114,1118 (1937)
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Ynamide-Mediated Intermolecular Esterification
Wang, Xuewei,Yang, Yang,Zhao, Yongli,Wang, Sheng,Hu, Wenchang,Li, Jinmei,Wang, Zihao,Yang, Fengling,Zhao, Junfeng
, p. 6188 - 6194 (2020/05/26)
An ynamide-mediated one-pot, two-step intermolecular esterification via the condensation of carboxylic acids with nucleophilic hydroxyl species was reported. A broad substrate scope with respect to carboxylic acids, alcohols, and phenols was observed. The α-acyloxyenamide intermediates formed by the addition of carboxylic acids to ynamides proved to be effective acylating reagents for the esterification of alcohol and phenol derivatives with the assistance of base catalysis. Notably, the racemization of the α-chiral center of carboxylic acids can be avoided.
The scope and regioselectivity of intramolecular N-C rearrangements of orthogonally protected sulfonamides, including cyclization to saccharin derivatives
Saidykhan, Amie,Ebert, Jenessa,Ally, Hashim,Gallagher, Richard T.,Martin, William H.C.,Bowen, Richard D.
supporting information, p. 3089 - 3091 (2017/07/18)
The scope and regiochemistry of the intramolecular N-C rearrangement involving ortholithiation of orthogonally protected sulfonamides in which an N-acyl or N-carboalkoxy group is transferred from nitrogen to the aromatic ring have been explored. Provided that excess lithium diisopropylamide is used, the process is compatible with the presence of acidic α-protons in a substituent attached to the aromatic ring or if the protons in the migrating acyl group are relatively inaccessible because of steric factors. In certain cases, the isolated product is not the ortho carboalkoxy species, but the derived saccharin; the regiochemistry found for starting materials containing a naphthalene ring is consistent with ortho lithiation at the most electron deficient position.
