408353-30-0Relevant academic research and scientific papers
Regioselective Synthesis of Substituted Carbazoles, Bicarbazoles, and Clausine C
Points, Gary L.,Beaudry, Christopher M.
supporting information, p. 6882 - 6885 (2021/09/11)
Substituted carbazoles are efficiently constructed from 3-triflato-2-pyrones and alkynyl anilines. Multiple substituents are tolerated on the carbazole, and complete control of regiochemistry is observed. Complicated and sterically congested substitution patterns are produced. This strategy is also used to prepare substituted bicarbazoles and related biaryls. Finally, the method was showcased in a synthesis of the carbazole natural product clausine C.
Nickel-catalyzed cyclization of 1,7-enynes for the selective synthesis of dihydrocyclobuta[c]quinolin-3-ones and benzo[b]azocin-2-ones
Cai, Yun,Chen, Fener,Hu, Yuanyuan,Jin, Hongwei,Li, Qiao,Liu, Yunkui,Zhou, Bingwei
supporting information, p. 11657 - 11660 (2021/11/12)
We herein described a nickel-catalyzed cyclization ofN-(o-ethynylaryl)acrylamides for the selective synthesis of dihydrocyclobuta[c]quinolin-3-ones and benzo[b]azocin-2-ones. The two varied products could be easily obtained by tuning the reaction temperature. This reaction features easy temperature-control, high efficiency, and gram-scale synthesis.
Transition-Metal Controlled Diastereodivergent Radical Cyclization/Azidation Cascade of 1,7-Enynes
Zhao, Yingying,Hu, Yancheng,Wang, Haolong,Li, Xincheng,Wan, Boshun
, p. 4412 - 4420 (2016/06/09)
A strategy for achieving diastereodivergent azidations of enynes has been developed, employing azide transfer from the M-N3 complex to alkyl radicals. Following this concept, the diastereoselectivity has been switched by modulating the transition metals and the ligands. The Mn(III)-mediated radical cyclization/azidation cascade of 1,7-enynes afforded trans-fused pyrrolo[3,4-c]quinolinones, whereas the Cu(II)/bipyridine system gave cis-products.
Synthesis and catalytic application of magnesium complexes bearing pendant indolyl ligands
Peng, Kuo-Fu,Chen, Yun,Chen, Chi-Tien
, p. 9610 - 9619 (2015/06/16)
Three novel indole-based ligand precursors [HIndPhR, R = methoxy, HIndPhOMe (2a); thiomethoxy, HIndPhSMe (2b); and N,N′-dimethylamino, HIndPhNMe2 (2c)] have been synthesized via Sonogashira and cyclization react
P-TsOH Promoted Au(I)-Catalyzed Consecutive Endo Cyclization of Yne-Tethered Ynamide: Access to Benzofused Dihydroisoquinolones
Nayak, Sanatan,Ghosh, Nayan,Prabagar,Sahoo, Akhila K.
supporting information, p. 5662 - 5665 (2015/12/01)
A novel synthetic route to benzo[f]dihydroisoquinolone through a p-TsOH promoted cascade cyclization of easily accessible diyne-tethered ynamides in the presence of a Au(I)-catalyst is described. This reaction unveils a broad substrate scope, constructing a wide range of benzo[f]dihydroisoquinolones in good yields. The diyne-tethered ynamides are synthesized from inexpensive o-iodoaniline through Sonogashira couplings and the Cu-mediated C-N bond formation. The role of p-TsOH is examined, and the reaction pathway is also deduced. The benzo[f]isoquinoline scaffold is constructed from benzo[f]dihydroisoquinolones.
Synthesis, characterization, and estrogen receptor binding affinity of flavone-, indole-, and furan-estradiol conjugates
Ahmed, Naseem,Dubuc, Celena,Rousseau, Jacques,Benard, Francois,van Lier, Johan E.
, p. 3212 - 3216 (2008/02/05)
Different flavone-, indole-, and furan-17β-estradiol conjugates, linked via alkyl spacer chains extending from the 17α-position of the estradiol moiety, were synthesized by Pd-catalyzed cross-coupling reactions. Structures were assigned based on spectrosc
Biradicals/zwitterions from thermolysis of enyne-isocyanates. Application to the synthesis of 2(1H)-pyridones, benzofuro[3,2-c]pyridin-1(2H)-ones, 2,5-dihydro-1H-pyrido[4,3,-b]indol-1-ones, and related compounds
Li, Hongbin,Yang, Hua,Petersen, Jeffrey L.,Wang, Kung K.
, p. 4500 - 4508 (2007/10/03)
Thermolysis of benzannulated enyne-isocyanates 13 and enyne-isocyanates 36 and 37 promoted the cycloaromatization reactions to generate in situ O,4-didehydro-2-hydroxyquinolines and O,4-didehydro-2-hydroxypyridines, respectively, as reactive intermediates. These cycloaromatized intermediates could be captured either as biradicals and/or as zwitterions depending on the nature of the substituent at the alkynyl terminus. The intermediate derived from cycloaromatization of 13a bearing a phenyl substituent could be regarded as biradical 14, which then abstracts hydrogen atoms from γ-terpinene leading to 2(1H)-quinolinone 15. Alternatively, the same intermediate could also be regarded as zwitterion 14′, which then undergoes an initial hydride abstraction from γ-terpinene followed by protonation to produce 15. The presence of a 2-phenylethyl substituent in 13b and 37a or a 2-methylphenyl substituent in 37b also allowed the resulting intermediates to be captured intramolecularly either as biradicals or as zwitterions, producing 2(1H)-quinolinone 19, 2(1H)-pyridone 39, and benzopyranopyridine 43, respectively. On the other hand, with a 2-methoxyphenyl, a 2-(dimethylamino) phenyl, or a 3-methoxypropyl substituent, the chemical behavior of the cycloaromatized adduct could be best accounted for in terms of a zwitterionic intermediate leading to benzofuro [3,2-c]quinolin-6(5H)-one (20), 5,11-dihydro-11-methyl-6H-indolo-[3,2-c]quinolin-6-one (25), benzofuro[3,2-c]pyridin-1(2H)-one 44, 2,5-dihydro-2,5-dimethyl-1H-pyrido-[4,3-b] indol-1-one 46, and related compounds. Interestingly, thermolysis of 37f bearing a 2-(methoxymethyl)phenyl substituent at the alkynyl terminus produced the unexpected benzopyranopyridine 56 as the major product in a process involving the cleavage of the bond between the methoxyl oxygen and the adjacent methylene carbon. The efficiency and selectivity of the cycloaromatization reaction could also be enhanced by the introduction of 1.1 to 10 equiv of dimethylphenylsilyl chloride to the reaction mixture to capture the resulting zwitterion.
