This article describes a method for synthesizing butyrolactone dimers using various inorganic silver salt catalysts.The method was successfully applied to alkyl 2-(2-bromopropyl)malonate 1,providing the dimeric butyro...This article describes a method for synthesizing butyrolactone dimers using various inorganic silver salt catalysts.The method was successfully applied to alkyl 2-(2-bromopropyl)malonate 1,providing the dimeric butyrolactone 2 when catalyzed by different silver salt catalysts.This synthesis method not only simplifies the original synthetic route,but also cleverly combines with natural product analogs,providing a strategy for the development of natural product polymer analogs in the future.展开更多
One-pot two-step stepwise reaction of terminal propargylic alcohols, carbon dioxide, and primary/secondary amines for the effective synthesis of various urethanes through robust silver-catalysed C-O/C-N bond formation...One-pot two-step stepwise reaction of terminal propargylic alcohols, carbon dioxide, and primary/secondary amines for the effective synthesis of various urethanes through robust silver-catalysed C-O/C-N bond formation is reported, Catalytic activities were investigated by controlling catalyst loading, reaction pressure and time, and very high turnover number (turnover frequency) was obtained: 3350 (35 h-1) with 0.01 mol% silver catalyst under 0.1 MPa, and up to 13360 (139 h-1) with 0.005 mol% silver catalyst under 2.0 MPa at room temperature. The strategy was ingeniously regulated, and synchronously afforded a wide range of β-oxopropylcarbamate and 1,3-oxazolidin-2-one motifs in excellent yields and selectivity together with unprecedented high turnover number (TON) and turnover frequency (TOF) value.展开更多
Disclosed herein is an efficient Ag-catalyzed 4+1 heteroannulation reaction of enamides withα-carbonyl sulfoxonium ylides.The diastereoselective transformation provides a practical access to a diverse range of multi-...Disclosed herein is an efficient Ag-catalyzed 4+1 heteroannulation reaction of enamides withα-carbonyl sulfoxonium ylides.The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives.The synthetic utility of the resultant tetrasubstituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.展开更多
The dual incorporation of two important functional groups—trifluoromethyl and cyano moieties into one heterocyclic core in a single-step reaction represents an appealing but largely unaddressed synthetic challenge.He...The dual incorporation of two important functional groups—trifluoromethyl and cyano moieties into one heterocyclic core in a single-step reaction represents an appealing but largely unaddressed synthetic challenge.Here we demonstrate that a silver-catalyzed[3+2]cycloaddition reaction of dicyanoalkenes with trifluorodiazoethane(CF_(3)CHN2)could render a facile construction of a unique category of pyrazoles that are simultaneously adorned by trifluoromethyl and cyano groups.Changing the location pattern of the cyano group in starting dicyanoalkene material allows regiodivergent access to two series of previously elusive trifluoromethyl cyanopyrazoles with an exquisite level of regiocontrol.Thus,this method could be applied in the preparation of cyano-analogues of CF_(3)-containing drugs(Celecoxib)and agrochemicals(Penthiopyrad and Fluazolate).Notably,several cyano-analogues of Celecoxib demonstrate enhanced inhibitory activity towards cyclooxygenase-2(COX-2),thereby laying a good foundation for developing new lead-based antiinflammatory agents.展开更多
A novel and facile synthesis of 4-arylquinolin-2(1H)-ones without metal catalysis has been developed.This reaction involved cyclization/elimination steps and was performed under metal-free conditions using inexpensi...A novel and facile synthesis of 4-arylquinolin-2(1H)-ones without metal catalysis has been developed.This reaction involved cyclization/elimination steps and was performed under metal-free conditions using inexpensive reagents such as NaI, selectfluor and KOH.展开更多
基金Project supported by the Natural Science Foundation of Shandong Province(No.ZR2021MB102).
文摘This article describes a method for synthesizing butyrolactone dimers using various inorganic silver salt catalysts.The method was successfully applied to alkyl 2-(2-bromopropyl)malonate 1,providing the dimeric butyrolactone 2 when catalyzed by different silver salt catalysts.This synthesis method not only simplifies the original synthetic route,but also cleverly combines with natural product analogs,providing a strategy for the development of natural product polymer analogs in the future.
基金We are grateful to the National Natural Science Foundation of China (21602232), the Natural Science Foundation for Youths of Shanxi (201701D221057), and the Project of "Utilization of Low Rank Coal" Strategic Leading Special Fund, Chinese Academy of Sciences (XDA-07070800, XDA-07070400).
文摘One-pot two-step stepwise reaction of terminal propargylic alcohols, carbon dioxide, and primary/secondary amines for the effective synthesis of various urethanes through robust silver-catalysed C-O/C-N bond formation is reported, Catalytic activities were investigated by controlling catalyst loading, reaction pressure and time, and very high turnover number (turnover frequency) was obtained: 3350 (35 h-1) with 0.01 mol% silver catalyst under 0.1 MPa, and up to 13360 (139 h-1) with 0.005 mol% silver catalyst under 2.0 MPa at room temperature. The strategy was ingeniously regulated, and synchronously afforded a wide range of β-oxopropylcarbamate and 1,3-oxazolidin-2-one motifs in excellent yields and selectivity together with unprecedented high turnover number (TON) and turnover frequency (TOF) value.
基金the National Natural Science Foundation of China(No.21702106)the Natural Science Foundation of Jiangsu Province(No.BK20170967)the Start-up Grant from Nanjing Tech University(No.39839101)for financial support。
文摘Disclosed herein is an efficient Ag-catalyzed 4+1 heteroannulation reaction of enamides withα-carbonyl sulfoxonium ylides.The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives.The synthetic utility of the resultant tetrasubstituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.
基金This work is supported by the National Natural Science Foundation of China(grant nos.92156025,21901181,and 21961142015)the National Key Research and Development Program of China(grant nos.2019YFA0905100 and 2021YFF0701700)Tianjin Municipal Science and Technology Commission(grant no.19JCQNJC04700).
文摘The dual incorporation of two important functional groups—trifluoromethyl and cyano moieties into one heterocyclic core in a single-step reaction represents an appealing but largely unaddressed synthetic challenge.Here we demonstrate that a silver-catalyzed[3+2]cycloaddition reaction of dicyanoalkenes with trifluorodiazoethane(CF_(3)CHN2)could render a facile construction of a unique category of pyrazoles that are simultaneously adorned by trifluoromethyl and cyano groups.Changing the location pattern of the cyano group in starting dicyanoalkene material allows regiodivergent access to two series of previously elusive trifluoromethyl cyanopyrazoles with an exquisite level of regiocontrol.Thus,this method could be applied in the preparation of cyano-analogues of CF_(3)-containing drugs(Celecoxib)and agrochemicals(Penthiopyrad and Fluazolate).Notably,several cyano-analogues of Celecoxib demonstrate enhanced inhibitory activity towards cyclooxygenase-2(COX-2),thereby laying a good foundation for developing new lead-based antiinflammatory agents.
基金financially supported by the National Natural Science Foundation of China(Nos.21302042 and 21172055)the Program for Innovative Research Team from Zhengzhou(No.131P-CXTD605)the Plan for Scientific Innovation Talent of Henan University of Technology(No.171147)
文摘A novel and facile synthesis of 4-arylquinolin-2(1H)-ones without metal catalysis has been developed.This reaction involved cyclization/elimination steps and was performed under metal-free conditions using inexpensive reagents such as NaI, selectfluor and KOH.