5693-54-9Relevant articles and documents
Synthesis and unusual stability of pyridine and N-methyl pyridinium 1,3-dioxolanes
Hobson, Stephen T.,Boecker, Joseph D.,Gifford, James H.,Nohe, Tara L.,Wierks, Carl H.
, p. 277 - 282 (2003)
Differentially substituted bridged pyridinium oximes are necessary in research on antidotes for organophosphate poisoning. A solid-phase synthesis would improve the yield and ease of purification of these compounds. To predict the lability of the linker in the final step of our proposed synthesis, we synthesized a series of pyridine and N-methyl pyridinium acetals. These compounds proved to be resistant to acid catalyzed hydrolysis. This stability may be useful for synthetic manipulation of pyridine aldehydes.
Total Synthesis of Cryptopleurine and Its Analogues
Takasu, Kiyosei,Tateishi, Kaito,Yamakawa, Takuro,Yamaoka, Yousuke
, (2022/03/08)
Total synthesis of phenanthroquinolizidine alkaloid cryptopleurine was achieved in 8 steps from commercially available 2-pyridinecarboxaldehyde and the epoxide derived from methyleugenol. The key intermediate vinyl triflate enables the divergent synthesis of cryptopleurine derivatives by late-stage installation of various substituents on the C-ring.
A bench-stable reagent for C-4 selective deuteriodifluoromethylation of azines
Dong, Lefeng,Kong, Yijin,Li, Zhong,Liang, Junqing,Qian, Feng,Shao, Xusheng,Wang, Mingxia,Xu, Xiaoyong
supporting information, (2022/03/16)
Deuteriodifluoromethyl (CF2D) is a challenging and important functional group due to difficult deuterium incorporation and lack of effective precursor reagents. Herein, we report a bench-stable reagent, deuteriodifluoromethyl phosphine (DDFP) from cheap deuterium source for selectivity deuteriodifluoromethylation of azines with a high deuterium incorporation yield. The late-stage modification of complex molecules further confirmed the potential of this reagent for practical applications. We expect that our reagent to find applications in synthesis of isotope-labelled molecules of interests for drug-discovery and related ilucidation of mechanism of action.
Supramolecular Metallacycles and Their Binding of Fullerenes
Ehnbom, Andreas,G?b, Christian R.,Oppel, Iris M.,Sturm, Lisa,Tobe, Yoshito
supporting information, (2020/03/19)
The synthesis of a new triaminoguanidinium-based ligand with three tris-chelating [NNO]-binding pockets and C3 symmetry is described. The reaction of tris-(2-pyridinylene-N-oxide)triaminoguanidinium salts with zinc(II) formate leads to the formation of cyclic supramolecular coordination compounds which in solution bind fullerenes in their spherical cavities. The rapid encapsulation of C60 can be observed by NMR spectroscopy and single-crystal X-ray diffraction and is verified using computation.
Benzoyl peroxide promoted radical ortho-alkylation of nitrogen heteroaromatics with simple alkanes and alcohols
Fang, Lei,Chen, Liangshun,Yu, Jianjun,Wang, Limin
supporting information, p. 1910 - 1914 (2015/03/18)
A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols leads to the corresponding 2-alkylpyridines with high regioselectivity in moderate to good yields without an additional reduction step to remove the activated group. A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols has been developed. The strategy allowed convenient access to various 2-alkylpyridines in moderate to good yields without an additional reduction step to remove the activated group.
Intermolecular reactions of chlorohydrine anions: Acetalization of carbonyl compounds under basic conditions
Barbasiewicz, Michal,Makosza, Mieczyslaw
, p. 3745 - 3748 (2007/10/03)
Nonenolizable aldehydes and ketones react with 2-chloroethanol and 3-chloropropanol under basic conditions (t-BuOK, DMF/THF) with formation of 2-substituted 1,3-dioxolanes and 1,3-dioxanes, respectively. Conversion of the two-step addition-alkylation process depends on the electrophilicity of the carbonyl group that governs the equilibrium of addition of chloroalkoxides. This method of protection of carbonyl groups in the form of cyclic acetals under kinetically controlled conditions is complementary to the acid-catalyzed reaction with diols.
Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay
Ponde, Datta E.,Deshpande, Vishnu H.,Bulbule, Vivek J.,Sudalai, Ammugam,Gajare, Anil S.
, p. 1058 - 1063 (2007/10/03)
Transesterification and transthiolesterification of β-keto esters with variety of alcohols and thiols and selective protection of carbonyl functions with various protecting groups catalyzed by natural kaolinitic clay are described. The clay has been found to be an efficient catalyst in transesterifying long chain alcohols, unsaturated alcohols, and phenols to give their corresponding β-keto esters in high yields. For the first time, transthiolesterification of β-keto esters with a variety of thiols has been achieved under catalytic conditions. Clay also catalyzes selective transesterification of β-keto esters by primary alcohols in the presence of secondary and tertiary alcohols giving corresponding β-keto esters. A systematic study involving the reactivity of different nucleophiles (alcohols, amines, and thiols) toward β-keto esters is also described. Sterically hindered carbonyl groups as well as α,β-unsaturated carbonyl groups underwent protection without the deconjugation of the double bond. Chemoselective protection of aldehydes in the presence of ketones has also been achieved over natural kaolinitic clay.
Substituted 6,11-ethano-6,11-dihydrobenzo[b] quinolizinium salts and compositions and methods of use thereof
-
, (2015/04/15)
Substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts, pharmaceutical compositions containing them, and methods for the treatment of neurodegenerative disorders or neurotoxic injuries utilizing them, wherein the substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts have the formula: STR1 wherein: R1, R2, R3, R4, R5, R6, R7, X and p are as defined in the specification.
Natural kaolinitic clay: A remarkable reusable solid catalyst for the selective functional protection of aldehydes and ketones
Ponde, Datta,Borate,Sudalai,Ravindranathan,Deshpande
, p. 4605 - 4608 (2007/10/03)
Natural kaolinitic clay possessing transition metals such as Fe and Ti in its lattice has been found to catalyze efficiently the chemoselective acetalization and thioacetalization of variety of carbonyl compounds with ethane - 1,2 - diol and ethane - 1,2 - dithiol respectively.
Reduction of n-(1,3-Dioxolan-2-yl)-1-methylpyridinium Ions: Molecular Structure of the 4-(1,3-Dioxolan-2-yl)-1-methyl-1,2,3,6-tetrahydropyridine-Borane Complex
Rodriguez, J. G.,Martinez-Lopez, N.,Lerma, J. Lopez de,Perales, A.
, p. 135 - 139 (2007/10/02)
The reduction of the n-(1,3-dioxolan-2-yl)-1-methylpyridinium ions with sodium borohydride has been studied to prepare N-methylformylpiperidines.Deuterium oxide was used as the solvent in order to assign the protons in the nmr spectra.As a product of the reaction, the 4-(1,3-dioxolan-2-yl)-1-methyl-1,2,3,6-tetrahydropyridine-borane complex, was isolated and crystallized.A X-ray study of this borane complex has been carried out.
