74929-23-0Relevant articles and documents
Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols
Man, Ningning,Li, Yuming,Jie, Jiyang,Li, Hongyun,Yang, Haijun,Zhao, Yufen,Fu, Hua
, p. 12884 - 12889 (2021/07/28)
Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.
Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde
Chen, Xiaojuan,Fu, Liping,Huo, Xiaoli,Shao, Jiaan,Yu, Liya,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang,Zhu, Huajian
, p. 16430 - 16433 (2021/10/01)
A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.
Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization
Zhou, Bingnan,Wu, Qiuyue,Dong, Ziyang,Xu, Jiaxi,Yang, Zhanhui
supporting information, p. 3594 - 3599 (2019/05/24)
A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6-endo-trig/dig cyclization are realized, giving structurally diverse 4H-thiopyran-4-ones and 2,3-dihydro-4H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications of our formal (3 + 3) transannulations in the structural modifications of natural products.
Gold-Catalyzed Synthesis of 2,5-Disubstituted Oxazoles from Carboxamides and Propynals
Xu, Yun,Wang, Qian,Wu, Yufeng,Zeng, Zhongyi,Rudolph, Matthias,Hashmi, A. Stephen K.
supporting information, p. 2309 - 2314 (2019/04/13)
2,5-Disubstituted oxazoles are synthesized by oxidative gold catalysis. In contrast to a reported procedure that delivers 2,4-disubstituted oxazoles starting from terminal alkynes, a switch in selectivity towards a 2,5-disubstitution is achieved by the use of propynals as starting materials. In the new reaction, the key intermediate is formed by the nucleophilic attack of the carboxamide onto a gold carbenoid, and then condensates with the more electrophilic aldehyde moiety already present in the substrate and not with the ketone that is derived from the oxygen donor. This new cyclization mode introduces a new carbonyl moiety as substituent at the 2,5-disubstituted oxazole, an attractive motive that can be found in bioactive compounds or be used for further derivatizations. (Figure presented.).
Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines
Chen, Zhengwang,Liang, Pei,Ma, Xiaoyue,Luo, Haiqing,Xu, Guohai,Liu, Tanggao,Wen, Xiaowei,Zheng, Jing,Ye, Hui
, p. 1630 - 1639 (2019/01/26)
A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.
Applications of Thermal Activation, Ball-milling and Aqueous Medium in Stereoselective Michael Addition of Nitromethane to Enynones Catalyzed by Chiral Squaramides
Ignatiuk, ?aneta A.,Janicki, Miko?aj J.,Góra, Robert W.,Konieczny, Krzysztof,Kowalczyk, Rafa?
, p. 1108 - 1116 (2019/01/30)
Stereoselective addition of nitromethane to conjugated en-ynones was performed through the application of chiral squaramides. Three non-classical approaches to promote the addition reaction were tested, including activation of the nucleophile by inorganic base in a biphasic aqueous system, thermal activation, and ball-milling. Hydrogen-bonding catalysis was effective in all these methods, providing 1,4-addition products in high yields and stereoselectivities of up to 98% requiring 1–5 mol% of Cinchona alkaloid squaramide. (Figure presented.).
Two-Step Synthesis of (Z)-3-Aryl-5-(arylmethylidene)butenolides by an Ivanov Reaction/Silver(I)-Catalyzed Lactonization/In Situ Dehydration Sequence
Hermann, David,Arican, Deniz,Brückner, Reinhard
, p. 326 - 352 (2016/12/24)
A stereoselective synthesis of the title compounds was developed. Hexane- and amine-free THF solutions of α-lithiated lithium arylacetates ('arylacetic acid dianions') were aldol-added to 3-arylpropynals. This gave 2,5-diaryl-3-hydroxypent-4-ynoic acids with up to a 72:28 preference for the anti-diastereomer (27 examples + 1 exception). When treated with Ag2CO3 (1-20 mol%) in DMF at room temperature for 2.5 days, the respective mixtures underwent regio- and stereoselective lactonizations followed by an in situ dehydration. Thereby 3-aryl-5-(arylmethylidene)butenolides were obtained with a Z-configuration of the oxygenated C=C bond. Their overall yields ranged from 46% to 83% (1 exception: 28%). Three 3-aryl-5-(arylmethylidene)butenolides contained a C-Br and/or a C-I bond. They allowed a subsequent Pd-catalyzed C-C coupling, which furnished follow-up butenolides.
Combining silver catalysis and organocatalysis: A sequential michael addition/hydroalkoxylation one-pot approach to annulated coumarins
Hack, Daniel,Chauhan, Pankaj,Deckers, Kristina,Hermann, Gary N.,Mertens, Lucas,Raabe, Gerhard,Enders, Dieter
supporting information, p. 5188 - 5191 (2014/12/11)
A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.
Zinc-catalyzed [4+3] cycloaddition with concomitant furan annulation: Formation of cyclohepta[b]furans
Song, Bo,Li, Lian-Hua,Song, Xian-Rong,Qiu, Yi-Feng,Zhong, Mei-Jin,Zhou, Ping-Xin,Liang, Yong-Min
, p. 5910 - 5913 (2014/05/20)
A convenient zinc-promoted [4+3] cycloaddition of a carbonyl ene-yne with simple dienes was first achieved. This reaction provided an efficient strategy to prepare various cyclohepta[b]furan rings by cascade cycloadditions. Additionally, a multicomponent reaction of dione, alkynal, and diene was also reported, which exhibited a novel strategy for selective creations of C-O bonds and C-C bonds. Go tandem! A first zinc-catalyzed tandem [4+3] cycloaddition is presented herein. Various substituted cyclohepta[b]furans were synthesized from carbonyl ene-yne and diene in moderate to good yield. Furan rings and seven-membered rings were prepared in one single step (see scheme; TBS=tert-butyldimethyl).
UNSATURATED HETEROCYCLIC INHIBITORS OF NECROPTOSIS
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Page/Page column 46, (2010/07/09)
The invention features new small molecule inhibitors of necroptosis. The compounds of the invention are described by Formulas (I) and (II). The invention also features pharmaceutical compositions that include compounds of Formula (I) and (II). The compounds and compositions of the invention are also featured in kits and in methods of treatment of conditions that include neurodegenerative diseases, ischemic brain and heart injuries, and head trauma.
