1632-48-0Relevant articles and documents
Synthesis of 1',2',3',4',5'-pentamethyl-3,4-diphenylazaferrocene and its enantioselective C-2 functionalization via (-)-sparteine-mediated lithiation
Fukuda, Tsutomu,Koga, Yasuyuki,Iwao, Masatomo
, p. 1237 - 1248 (2008)
Lithiation of 1',2',3',4',5'-pentamethyl-3,4-diphenylazaferrocene (9) with sec-BuLi/(-)-sparteine (2) in Et2O at -78 °C followed by quenching with electrophiles gave the C-2 functionalized azaferrocenes (17) in good enantioselectivities (up to
Copper-catalyzed double N-alkenylation of amides: An efficient synthesis of di- or trisubstituted N-acylpyrroles
Yuan, Xiyuan,Xu, Xiaobing,Zhou, Xiaobo,Yuan, Jiwei,Mai, Lugen,Li, Yanzhong
, p. 1510 - 1513 (2007)
(Chemical Equation Presented) An efficient copper-catalyzed double alkenylation of amides with (1Z,3Z)-1,4-diiodo-1,3-dienes is reported for the first time. The reactions proceed to afford di- or trisubstituted N-acylpyrroles in good to excellent yields using CuI as the catalyst, Cs2CO 3 as the base, and rac-trans-N,N′-dimethylcyclohexane-1,2- diamine as the ligand.
A supramolecular photocatalyst composed of a polyoxometalate and a photosensitizing water-soluble porphyrin diacid for the oxidation of organic substrates in water
Ishizuka, Tomoya,Ohkawa, Shumpei,Ochiai, Hidemi,Hashimoto, Muneaki,Ohkubo, Kei,Kotani, Hiroaki,Sadakane, Masahiro,Fukuzumi, Shunichi,Kojima, Takahiko
, p. 1975 - 1980 (2018)
A diprotonated form of a cationic water-soluble saddle-distorted porphyrin (H416+) forms stable supramolecular assemblies with multianionic polyoxometalates (POMs) by electrostatic interactions. An assembly of H416+ with a Ru-substituted POM can perform photocatalytic oxidation of organic substrates in water under visible-light irradiation through adduct formation of the H416+ moiety with an oxidant.
Structure-activity relationships study of neolamellarin A and its analogues as hypoxia inducible factor-1 (HIF-1) inhibitors
Li, Guangzhe,Dong, Huijuan,Ma, Yao,Shao, Kun,Li, Yueqing,Wu, Xiaodan,Wang, Shisheng,Shao,Zhao, Weijie
supporting information, p. 2327 - 2331 (2019/07/09)
The novel marine pyrrole alkaloid neolamellarin A derived from sponge has been shown to inhibit hypoxia-induced HIF-1 activity. In this work, we designed and synthesized neolamellarin A and its series of derivatives by a convergent synthetic strategy. The HIF-1 inhibitory activity and cytotoxicity of these compounds were evaluated in Hela cells by dual-luciferase reporter gene assay and MTT assay, respectively. The results showed that neolamellarin A 1 (IC50 = 10.8 ± 1.0 μM) and derivative 2b (IC50 = 11.9 ± 3.6 μM) had the best HIF-1 inhibitory activity and low cytotoxicity. Our SAR research focused on the effects of key regions aliphatic carbon chain length, aromatic ring substituents and C-7 substituent on biological activity, providing a basis for the subsequent research on the development of novel pyrrole alkaloids as HIF-1 inhibitors and design of small molecule probes for target protein identification.
Diprotonated [28]hexaphyrins(1.1.1.1.1.1): Triangular antiaromatic macrocycles
Ishida, Shin-Ichiro,Higashino, Tomohiro,Mori, Shigeki,Mori, Hirotaka,Aratani, Naoki,Tanaka, Takayuki,Lim, Jong Min,Kim, Dongho,Osuka, Atsuhiro
supporting information, p. 3427 - 3431 (2014/04/03)
Protonation of meso-aryl [28]hexaphyrins(1.1.1.1.1.1) triggered conformational changes. Whereas protonation with trifluoroacetic acid led to the formation of monoprotonated Moebius aromatic species, protonation with methanesulfonic acid led to the formati
A Paal-Knorr approach to 3,4-diaryl-substituted pyrroles: Facile synthesis of lamellarins O and Q
Ramirez-Rodriguez, Armando,Mendez, Jose M.,Jimenez, Cristina C.,Leon, Fernando,Vazquez, Alfredo
, p. 3321 - 3326,6 (2012/12/12)
A very simple, yet efficient synthetic methodology, to obtain 3,4-diaryl-substituted pyrroles is described. The approach is based on the Knoevenagel condensation between arylacetonitriles and substituted aromatic aldehydes, followed by conjugate addition of cyanide to afford succinonitriles in excellent yields. The products thus obtained were subjected to DIBAL-H reduction, followed by cyclization under acidic conditions to produce the corresponding pyrroles in good overall yields. The utility of this protocol is exemplified by the synthesis of the marine alkaloids lamellarins O and Q.
2,4- vs 3,4-disubsituted pyrrole synthesis switched by copper and nickel catalysts
Chen, Feng,Shen, Tao,Cui, Yuxin,Jiao, Ning
supporting information, p. 4926 - 4929,4 (2012/12/12)
A novel and efficient copper or nickel catalyzed highly selective denitrogenative annulation of vinyl azides with aryl acetaldehydes has been developed. 2,4- and 3,4-diaryl substituted pyrroles, which are difficult to synthesize by the reported methods, can be highly regioselectively prepared by this protocol simply switched by the selection of the transition metal catalysts. Compared with the reported acidic or basic conditions for polysubstituted pyrrole synthesis, the present reaction conditions are mild, neutral, and very simple without any additives.
One-pot AgOAc-mediated synthesis of polysubstituted pyrroles from primary amines and aldehydes: Application to the total synthesis of purpurone
Li, Qingjiang,Fan, Aili,Lu, Zhiyao,Cui, Yuxin,Lin, Wenhan,Jia, Yanxing
supporting information; experimental part, p. 4066 - 4069 (2010/11/16)
A simple and efficient method for the synthesis of 1,3,4-trisubstituted or 3,4-disubstituted pyrroles has been developed. The reaction represents the first time that pyrroles are synthesized directly from readily available aldehydes and amines (anilines)
Multiple conformational changes of β-tetraphenyl meso- hexakis(pentafluorophenyl) substituted [26] and [28]hexaphyrins(1.1.1.1.1.1)
Koide, Taro,Youfu, Katsuyuki,Saito, Shohei,Osuka, Atsuhiro
supporting information; experimental part, p. 6047 - 6049 (2010/11/05)
β-Tetraphenyl meso-hexakis(pentafluorophenyl) substituted [26]hexaphyrin 3 is conformationally flexible between rectangular and figure-of-eight shapes and its two-electron reduced [28]hexaphyrin 4 takes figure-of-eight conformations, which are changed, up
Copper-catalyzed synthesis of five-membered heterocycles via double C-N bond formation: an efficient synthesis of pyrroles, dihydropyrroles, and carbazoles
Li, Ende,Xu, Xiaobing,Li, Hongfeng,Zhang, Huimin,Xu, Xiaolei,Yuan, Xiyuan,Li, Yanzhong
scheme or table, p. 8961 - 8968 (2009/12/24)
An efficient copper-catalyzed double C-N bond forming reaction using diiodides and nitrogen-centered nucleophiles including amides and carbamates is reported. The reactions proceed to afford di- or tri-substituted N-acylpyrroles, dihydropyrroles, and carbazoles in good to excellent yields when different diiodides such as 1,4-diiodo-1,3-butadienes, 1,4-dihalobut-1-enes, and 2,2′-diiodobiphenyls were employed, respectively. It is crucial to use CuI as the catalyst with the assistance of proper base and diamine ligand.
