36982-91-9Relevant academic research and scientific papers
Isothiourea-Catalyzed Enantioselective Synthesis of Tetrahydro-α-carbolinones
Liu, Honglei,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 1301 - 1305 (2020/02/25)
An isothiourea-catalyzed enantioselective annulation protocol using indolin-2-imines with a series of α,β-unsaturated p-nitrophenyl esters for the synthesis of tetrahydro-α-carbolinones was developed. Using 5 mol % of the isothiourea HyperBTM as the Lewis base catalyst, this process allows the enantioselective preparation of a range of C(4)-substituted tetrahydro-α-carbolinones in good to excellent yield and with high enantioselectivity (20 examples, 32-99% yield and up to 99:1 er).
Palladium(0)-Catalyzed Carbonylative Synthesis of N-Acylsulfonamides via Regioselective Acylation
Schembri, Luke S.,Eriksson, Jonas,Odell, Luke R.
, p. 6970 - 6981 (2019/06/14)
N-Acylsulfonamides represent an important bioisostere of carboxylic acids that allow for greater molecular elaboration and enhanced hydrogen bonding capabilities. Herein, we present a mild and convenient palladium(0)-catalyzed synthesis of N-acylsulfonamides via the carbonylative coupling of sulfonyl azides and electron-rich heterocycles. The reaction proceeds via in situ generation of a sulfonyl isocyanate followed by regioselective acylation of an indole or pyrrole nucleophile. This approach has been used to synthesize 34 indole- and pyrrole-substituted N-acylsulfonamides in yields of up to 95%. Importantly, this process is ligand-free and compatible with an ex situ solid CO source and requires only slightly elevated temperatures, making it a highly attractive method for the preparation of this important class of compounds. This study further investigated the possibility of labeling N-acylsulfonamides with carbon-11 to facilitate biological evaluation and in vivo studies with positron emission tomography.
Preparation of 3-diazoindolin-2-imines via cascade reaction between indoles and sulfonylazides and their extensions to 2,3-diaminoindoles and imidazo[4,5-b]indoles
Sheng, Guorong,Huang, Kai,Chi, Zhihao,Ding, Hualong,Xing, Yanpeng,Lu, Ping,Wang, Yanguang
supporting information, p. 5096 - 5099 (2014/12/11)
3-Diazoindolin-2-imines were constructed from indoles and sulfonylazides via an electronically matched 1,3-dipolar cycloaddition and a subsequent dehydroaromatization/ring-opening cascade. The reaction between 3-substituted indoles and sulfonyl azides provided 2-aminoindoles, while 2-substituted indoles furnished 3-aminoindoles. Moreover, 2,3-diaminoindoles could be prepared from the resulting 3-diazoindolin-2-imines and secondary amines via a rhodium-catalyzed amination. Further extension of 2,3-diaminoindoles led to the formation of imidazo[4,5-b]indoles.
Preparation of triazoloindoles via tandem copper catalysis and their utility as α-imino rhodium carbene precursors
Xing, Yanpeng,Sheng, Guorong,Wang, Jing,Lu, Ping,Wang, Yanguang
, p. 1244 - 1247 (2014/03/21)
3-Sulfonyl[1,2,3]triazolo[4,5-b]indoles were efficiently prepared via a tandem catalysis process involving intramolecular ligand stabilized CuAAC and Cu-catalyzed C-N coupling. The obtained 3-sulfonyl[1,2,3]triazolo[4,5-b]indoles could be utilized as α-im
A new route to indolines by the cu-catalyzed cyclization reaction of 2-ethynylanilines with sulfonyl azides
Yoo, Eun Jeong,Chang, Sukbok
supporting information; experimental part, p. 1163 - 1166 (2009/04/06)
It is revealed that 2-sulfonyliminoindolines can be efficiently synthesized by the Cu-catalyzed cyclization reaction of N-alkyl-or aryl-substituted 2-ethynylanilines with sulfonyl azides. This new route to the indoline derivatives is characterized by mild
