253435-19-7Relevant academic research and scientific papers
Copper-catalysed three-component carboiodination of arynes: Expeditious synthesis of: O -alkynyl aryl iodides
Cao, Wenxuan,Niu, Sheng-Li,Shuai, Li,Xiao, Qing
supporting information, p. 972 - 975 (2020/02/03)
A copper-catalysed three-component iodoalkynylation reaction of arynes for the expeditious and versatile synthesis of o-alkynyl aryl iodides has been developed. Mechanism research shows that the reaction goes through two steps enabled by copper catalysis: the formation of 1-iodo-2-arylacetylene and the insertion of the aryne into a C(sp)-I bond.
TBAI/TBHP-Mediated Cascade Cyclization toward Sulfonylated Indeno[1,2-c]quinolines
Meesin, Jatuporn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Leowanawat, Pawaret,Saithong, Saowanit,Kuhakarn, Chutima
supporting information, p. 6546 - 6549 (2017/12/26)
Treatment of ortho-amino-substituted aryldiyne derivatives with sulfonyl hydrazides in the presence of tetrabutylammonium iodide (TBAI) and tert-butyl hydroperoxide (TBHP) led to a cascade cyclization reaction to yield sulfonylated indeno[1,2-c]quinolines
Complex Annulations through Silver Carbenoid Intermediate: An Alternative Entry to Transformations of 1,2,3-Triazoles
Yang, Yuan,Yu, Jiang-Xi,Ouyang, Xuan-Hui,Li, Jin-Heng
, p. 3982 - 3985 (2017/08/14)
An alternative entry to transformations of N-sulfonyl-4-(2-(ethynyl)aryl)-1,2,3-triazoles with various generated in situ or external nucleophiles by means of silver catalysis for producing diverse functionalized isoquinolines is described. Mechanistically
Regioselective 5-endo-dig Electrophilic Iodocyclization of Enediynes: A Convenient Route to Iodo-substituted Indenes and Cyclopenta-Fused Arenes
Saunthwal, Rakesh K.,Danodia, Abhinandan K.,Patel, Monika,Kumar, Sushil,Verma, Akhilesh K.
supporting information, p. 3001 - 3007 (2016/11/13)
An efficient iodine-mediated regioselective tandem approach for the synthesis of symmetric and asymmetric iodo-substituted indenes and stereoselective cyclopenta [b]pyridine/thiophenes from easily accessible enediynes that proceeds by in situ formation of an iodonium intermediate followed by a regioselective 5-endo-dig cyclization has been described. The intramolecular electrophilic iodocyclization was selectively triggered by a distribution of electronic density along the alkyne bond. Subsequently, the iodo-substituted indenes were diversified by employing palladium-catalyzed cross-coupling reactions and the coupled products were further confirmed by X-ray crystallographic studies.
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.
, 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.
Diaceno[a,e]pentalenes from homoannulations of o-alkynylaryliodides utilizing a unique Pd(OAc)2/n-Bu4NOAc catalytic combination
Shen, Junjian,Yuan, Dafei,Qiao, Yan,Shen, Xingxing,Zhang, Zhongbo,Zhong, Yuwu,Yi, Yuanping,Zhu, Xiaozhang
, p. 4924 - 4927 (2015/04/27)
A heterogeneous catalytic system, Pd(OAc)2/n-Bu4NOAc, for the efficient synthesis of diaceno[a,e]pentalenes via a tandem Pd catalytic cycle is reported. The catalytic partner n-Bu4NOAc played indispensable and versatile ro
Synthesis of tetracyclic chromenones via platinum(ii) chloride catalysed cascade cyclization of enediyne-enones
Sivaraman, Mahalingam,Perumal, Paramasivan T.
, p. 1318 - 1327 (2014/03/21)
PtCl2 catalysed cascade cyclization of an enediyne-enone system to afford a tetracyclic chromenone is reported, which proceeds through two consecutive highly regioselective 6-endo-dig cyclizations in a single step with the formation of two new C-C bonds and two new rings in excellent yield. A mechanism for this transformation is proposed based on the isolated intermediates.
Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes
Prasad,Sekar
supporting information, p. 1659 - 1665 (2013/03/28)
A new copper-catalyzed in situ generation of aryl thiolates strategy was successfully developed for the one-pot synthesis of substituted benzothiazoles from 2-iodoanilides using xanthate as a thiol precursor. A wide range of 2-iodoanilides with both electron-releasing and electron-withdrawing groups produced the corresponding benzothiazoles in good yields. Further, this one-pot protocol was successfully utilized for the synthesis of a potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzo[d]thiazole (PMX 610). Finally, the copper-catalyzed in situ generation of aryl thiolates strategy was successfully applied for the domino synthesis of substituted benzothiophenes from o-haloalkynyl benzenes using xanthate as a thiol precursor.
A direct anionic cyclization of 2-alkynylbenzonitrile to 3- substituted-1(2H)-isoquinolones and 3-benzylideneisoindol-2ones initiated by methoxide addition
Wu, Ming-Jung,Chang, Li-Juan,Wei, Li-Mei,Lin, Chi-Fong
, p. 13193 - 13200 (2007/10/03)
Treatment of 2-(2-alkylethynyl)benzonitrile with sodium methoxide in refluxing methanol for 12 h gave 3-alkyl-1(2H)- isoquinolone in modest yield. Under the same reaction conditions, methanolysis of 2-(2-arylethynyl)benzonitrile lead to the formation of 3
