64793-76-6Relevant academic research and scientific papers
Synthesis and physico-chemical properties of porphycenes
Brenner, Wolfgang,Malig, Jenny,Oelsner, Christian,Guldi, Dirk M.,Jux, Norbert
, p. 651 - 662 (2012)
A new and improved synthesis for porphycenes is presented. In particular, treating pyrroles with iodine monochloride results in quantitative yields and easier work up. This key step was employed for the synthesis of different 2,7,12,17-substituted porphycenes (TPrPc, TPPc, TtBPPc). The synthetic part of this project is followed by a global analysis of the physico-chemical properties of three exemplary porphycenes, including absorption, emission, and electrochemistry. In-situ UV-vis/nIR spectroelectrochemistry was used to determine the spectral signatures of the radical anion and cation species. Temperature-dependent fluorescence lifetimes were determined under air as well as under inert atmosphere.
3+3 -cycloaddition reactions of α-acidic isocyanides with 1,3-dipolar azomethine imines
Du, Juan,Xu, Xianxiu,Li, Yifei,Pan, Ling,Liu, Qun
, p. 4004 - 4007 (2014)
α-Acidic isocyanides are versatile reagents in organic synthesis, especially for the synthesis of five-membered heterocycles via [3 + 2]-cycloaddition reactions with activated multiple bonds. In this communication, the first [3 + 3]-cross-cycloaddition of α-acidic isocyanides with 1,3-dipolar azomethine imines to generate a series of 1,2,4-triazine derivatives with significant regiochemical control under mild catalytic reaction conditions is described. This new strategy shows that α-acidic isocyanides can also be taken as potent reagents for the synthesis of six-membered heterocycles through [3 + 3]-cross-cycloaddition reactions with 1,3-dipoles.
Copper-Catalyzed Synthesis of Polysubstituted Pyrroles through [3+1+1] Cycloaddition Reaction of Nitrones and Isocyanides
Tian, Zhuang,Xu, Jiaojiao,Liu, Bingxin,Tan, Qitao,Xu, Bin
, p. 2603 - 2606 (2018/05/22)
An efficient, copper-catalyzed [3+1+1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting polysubstituted pyrroles from easily available nitrones and α-acidic isocyanides. The given approach features a new mo
Silver-catalyzed isocyanide-alkyne cycloaddition: A general and practical method to oligosubstituted pyrroles
Liu, Jianquan,Fang, Zhongxue,Zhang, Qian,Liu, Qun,Bi, Xihe
supporting information, p. 6953 - 6957 (2013/07/25)
Ag2CO3 is the key: The transition-metal-catalyzed cycloaddition of isocyanides and unactivated terminal alkynes has been realized with Ag2CO3 as a unique and robust catalyst (see scheme). The protocol is highly
Synthesis of pyrroles by click reaction: Silver-catalyzed cycloaddition of terminal alkynes with isocyanides
Gao, Meng,He, Chuan,Chen, Hongyi,Bai, Ruopeng,Cheng, Ben,Lei, Aiwen
supporting information, p. 6958 - 6961 (2013/07/25)
Just click with silver: Pyrroles are prepared by the co-cyclization of terminal alkynes and isocyanides in a silver-catalyzed click reaction. This route represents an extremely simple, efficient, and atom-economic approach to substituted pyrroles in good yields with high selectivity, thus complementing the click method for the rapid formation of multifunctional heterocycles. Copyright
Remarkable solvent effect in Barton-Zard pyrrole synthesis: application in an efficient one-step synthesis of pyrrole derivatives
Bhattacharya, Apurba,Cherukuri, Sankara,Plata, Robert Erik,Patel, Nitinchandra,Tamez Jr., Victoriano,Grosso, John A.,Peddicord, Michael,Palaniswamy, Venkatapuram A.
, p. 5481 - 5484 (2007/10/03)
A unique solvent effect encountered in the Barton-Zard pyrrole synthesis was exploited to develop an efficient synthesis of pyrrole-2-esters. The chemistry was extended to a one-pot synthesis of pyrrole-2,4-dicarboxylates.
Copper- or phosphine-catalyzed reaction of alkynes with isocyanides. Regioselective synthesis of substituted pyrroles controlled by the catalyst
Kamijo, Shin,Kanazawa, Chikashi,Yamamoto, Yoshinori
, p. 9260 - 9266 (2007/10/03)
The copper-catalyzed reaction of isocyanides (CNCH2EWG 1) 1 with electron-deficient alkynes (RC=CEWG2) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded
Preparation of pyrrole-2-carboxylates with electron-withdrawing groups at the 4-position
Uno, Hidemitsu,Tanaka, Masanori,Inoue, Takashi,Ono, Noboru
, p. 471 - 474 (2007/10/03)
Reaction of α-trifluoromethyl, α-cyano, and α-ethoxycarbonyl alkenyl sulfones with ethyl isocyanoacetate in the presence of a base gave 4- substituted pyrrole-2-carboxylates in moderate to good yields.
