1027223-97-7Relevant academic research and scientific papers
Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite- Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides
Senadi, Gopal Chandru,Wang, Ji-Qi,Gore, Babasaheb Sopan,Wang, Jeh-Jeng
, p. 2747 - 2753 (2017)
An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) [Pd(dba)2]/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transfo
A new synthesis of indoles via intramolecular cyclization of ?-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO
Chen, Yan-Yan,Chen, Jia-Hua,Zhang, Niu-Niu,Ye, Lin-Miao,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 478 - 481 (2015/03/05)
2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of ?-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOt-Bu in DMSO at room temperature. A reaction mechanism involving α-
A new synthesis of indoles via intramolecular cyclization of ο-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO
Chen, Yan-Yan,Chen, Jia-Hua,Zhang, Niu-Niu,Ye, Lin-Miao,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 478 - 481 (2015/04/27)
2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of ο-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOt-Bu in DMSO at room temperature. A reaction mechanism involving α-
Scaffold-divergent synthesis of ring-fused indoles, quinolines, and quinolones via iodonium-induced reaction cascades
Halim, Rosliana,Aurelio, Luigi,Scammells, Peter J.,Flynn, Bernard L.
, p. 4708 - 4718 (2013/06/27)
N-(2-Iodophenyl)imines A are readily formed from Schiff's base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.
Potassium tert-butoxide promoted intramolecular arylation via a radical pathway
Roman, Daniela Sustac,Takahashi, Yoko,Charette, Andre B.
supporting information; experimental part, p. 3242 - 3245 (2011/08/02)
Potassium tert-butoxide mediated intramolecular cyclization of aryl ethers, amines, and amides was efficiently performed under microwave irradiation to provide the corresponding products in high regioisomeric ratios. The reaction proceeds via single-electron transfer to initiate the formation of an aryl radical, followed by a kinetically favored 5-exo-trig and subsequent ring expansion.
Alternating lodonium-mediated reaction cascades giving indole- And quinoline-containing polycycles
Halim, Rosliana,Scammells, Peter J.,Flynn, Bernard L.
supporting information; experimental part, p. 1967 - 1970 (2009/04/10)
A simple two-step convergent protocol gives direct access to synthetic Intermediate A from ortho-iodoanilines. Intermediate A can be treated with NIS In CH2CI2 to Induce novel lodonium mediated domino reaction cascade, which provides direct access to ring-fused Indole compounds B. Simply by changing the reaction conditions, this protocol can be directed down an alternative domino reaction cascade to give various ring fused quinoline compounds C.
Development of an Efficient Procedure for Indole Ring Synthesis from 2-Ethynylaniline Derivatives Catalyzed by Cu(II) Salts and Its Application to Natural Product Synthesis
Hiroya, Kou,Itoh, Shin,Sakamoto, Takao
, p. 1126 - 1136 (2007/10/03)
The development of efficient methods for the indole synthesis catalyzed by Cu(II) salts and its applications were investigated. Cu(OAc)2 has been proved to be the best catalyst for the synthesis of various 1-p-tolylsulfonyl or 1-methylsulfonylindoles, which have both electron-withdrawing and electron-donating groups on the aromatic ring and C2 position of indoles. For the primary aniline derivatives, Cu(OCOCF 3)2 showed good activities, while Cu(OAc)2 was a good catalyst for the cyclization of secondary anilines. This methodology could be applied to the sequential cyclization reaction for the compounds which have the electrophilic part in the same molecule. By prior treatment with KH, the sequential cyclization was realized to provide the tricyclic ring systems, but it was limited to five- and six-membered rings for the second cyclization. Finally, formal and total synthesis of hippadine with the Cu(II)-promoted indole synthesis as the key step was accomplished.
