853-36-1Relevant articles and documents
Synthesis of polysubstituted pyrroles via Pd-catalyzed oxidative alkene C-H bond arylation and amination
Zheng, Jia,Huang, Liangbin,Huang, Chuyu,Wu, Wanqing,Jiang, Huanfeng
, p. 1235 - 1242 (2015/01/30)
A novel Pd(II)-catalyzed oxidative approach to construct polysubstituted pyrroles from N-homoallylicamines and arylboronic acids was developed. This transformation is supposed to proceed through cascade formation of C-C and C-N bonds via oxidative arylation of unactive alkenes, followed by intramolecular aza-Wacker cyclization.
One-pot synthesis of quinoline derivatives directly from terminal alkynes via sequential ruthenium(II) and acid catalysis
Zhang, Min,Roisnel, Thierry,Dixneufc, Pierre H.
body text, p. 1896 - 1903 (2010/11/05)
A convenient one-pot synthesis of 2,3-di- substituted, 2,3,6- trisubstituted, and 2,3,6,7-tetrasubstituted quinoline analogues from terminal alkynes via sequential ruthenium(II) and para-toluenesulfonic acid (p-TSA) co-catalyzed reactions is described. The catalytic process is shown to take place first via intermediate formation of an allyl ketone and then addition of an aniline derivative to the allyl ketone. The p-TSA is a catalyst for both allyl ketone and quinoline synthetic steps. The method allowed us to synthesize a wide range of quinoline derivatives and introduce different substituents by employing various simple starting materials. The reaction allows the synthesis of halogen-containing products.
Photochemistry of N-heterocycles. 7: Light induced reductive ring contractions of sixmembered cyclic iminium ions
Nagy, Jozsef,Madarasz, Zoltan,Rapp, Rudolf,Szoelloesy, Aron,Nyitrai, Jozsef,Doepp, Dietrich
, p. 281 - 290 (2007/10/03)
Photochemically induced reductive ring contractions, previously observed for 2,5-dihydro-1,2,4-triazines, have also been verified for 1,4-dihydropyrimidines 2a,b, the dihydro-1,2,4,5-tetrazine 9, and dihydro-1,3,5-triazines 11a,b giving rise to fivemembered fully unsaturated heterocycles (pyrroles 4a,b, imidazoles 13a,b, and triazole 10, respectively). The 1,4-dihydropyrazines 15a-j tend to decompose in acidified 2-propanol in the dark, but on irradiation they also undergo reductive ring contraction furnishing solely the 1,2,5-triarylpyrroles 16a-d rather than the (a priori also possible) isomeric 1,3,4-triarylpyrroles 17a-d. In contrast, the 3,6-diphenylpyrid-azine 18 gives the 4-isopropyl-analogue 19 in low yield upon irradiation in hydrogen chloride saturated 2-propanol. Wiley-VCH Verlag GmbH, 2000.