2471-70-7Relevant articles and documents
-
Haworth,Sheldrick
, p. 864,866 (1934)
-
Steric Factors in Amide-Directed Metalations of N,N-Dialkyl-6-methoxynaphthalene-2-carboxamides: Synthesis of a Sterically Perturbed Acylnaphthol
Bindal, Rajeshwar D.,Katzenellenbogen, John A.
, p. 3181 - 3185 (1987)
The powerful ortho-metalating directive effect of the N,N-dialkylcarboxamide group can be used for the preparation of C-1 alkyl-substituted 2,6-acylnaphthols.The alternative reaction pathways of C-1 metalation vs. acylation (carbonyl addition) in the reaction of alkyllithium reagents with N,N-dialkyl-6-methoxy-naphthalenecarboxamides depends upon the cumulative steric nature of the N-alkyl and lithium alkyl groups: The N,N-dimethylamide 7 undergoes carbonyl addition with n-BuLi and t-BuLi; the N,N-diethylamide 8, carbonyl addition with n-BuLi, but metalation with t-BuLi; and the N,N-diisopropylamide 9 only C-1 metalation with n-BuLi.Subsequent reaction of the N,N-diethyl-1-ethyl-6-methoxynaphhtalene-2-carboxamide (13) with n-BuLi gives the desired 2,6-acylnaphthyl methyl ether, whereas the corresponding ethylated diisopropylamide 14 undergoes additional metalation on the ethyl group.These 1-ethyl-2-carboxamidonaphthalenes are very sterically crowded and show evidence in the proton NMR of hindered rotation about both the amide bond and the ethyl group.The UV and fluorescence spectra of the acylnaphthols 17 and 18 show the consequences of this steric crowding through reduced conjugation between the acyl group and the naphthalene group.The more hindered 1-ethylated acylnaphthol 18 shows lower molar absorptivity, and it fluoresces only in basic solution.
Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts
Bhunia, Samir Kumar,Das, Pritha,Nandi, Shantanu,Jana, Ranjan
supporting information, p. 4632 - 4637 (2019/06/27)
We report herein a visible-light-promoted, highly practical carboxylation of readily accessible aryl triflates at ambient temperature and a balloon pressure of CO2 by the combined use of palladium and photoredox Ir(III) catalysts. Strikingly, the stoichiometric metallic reductant is replaced by a nonmetallic amine reductant providing an environmentally benign carboxylation process. In addition, one-pot synthesis of a carboxylic acid directly from phenol and modification of estrone and concise synthesis of pharmaceutical drugs adapalene and bexarotene have been accomplished via late-stage carboxylation reaction. Furthermore, a parallel decarboxylation-carboxylation reaction has been demonstrated in an H-type closed vessel that is an interesting concept for the strategic sector. Spectroscopic and spectroelectrochemical studies indicated electron transfer from the Ir(III)/DIPEA combination to generate aryl carboxylate and Pd(0) for catalytic turnover.
The influence of the thioalkyl terminal group on the mesomorphic behavior of some 6-alkoxy-2-naphthoates derived from 1,3,4-oxadiazole
Chothani,Akbari,Patel,Patel
, p. 31 - 46 (2016/07/21)
A new series of mesogenic compounds having a naphthalene moiety has been synthesized by esterification of 4-(5-(alkyllthio)-1,3,4-oxadiazol-2-yl)phenol and 6-alkoxy-2-naphthoic acid and their liquid crystalline properties have been studied. All the members of the series are enantiotropic and exhibit smectic as well as nematic mesophase. The plot of transition temperatures versus number of carbon atoms in the alkoxy chain exhibits no odd even effect and falling tendency for isotropic transition temperatures. High anisotropy, linearity confers rich mesomorphic properties on the system.
An improved protocol for the oxidative cleavage of alkynes, alkenes, and diols with recyclable Ru/C
Vijay Kumar,Prakash Reddy,Sridhar,Srinivas,Rama Rao
experimental part, p. 739 - 742 (2009/07/18)
Efficient synthesis of carboxylic acids from alkynes; aldehydes from alkenes and diols employing Ru/C-based recyclable catalytic system is reported with good to excellent yields. Georg Thieme Verlag Stuttgart.
