52762-77-3Relevant articles and documents
Synthesis of functionalised furans and pyrroles through annulation reactions of 4-pentynones
Arcadi, Antonio,Rossi, Elisabetta
, p. 15253 - 15272 (2007/10/03)
A new approach to 4-pentynones through palladium-catalysed coupling reaction of the ready available 2-propynyl ketones with aryl iodides and/or vinyl triflates is proposed. Annulation reactions of both 2-propynyl ketones and 4-pentynones gave functionalised furans using potassium tert-butoxide in DMF and functionalised pyrroles in the presence of benzylamine or ammonia, respectively in good to high yields. The methodology has been extended to the preparation of 17β-hydroxyandrost-4-en[3,2-b](5-methyl)furan and to 17β- hydroxyandrost-4-en[3,2-b](1-benzyl-5-methyl)pyrrole. A different reaction pattern was observed when the 4-pentynones were treated with sodium methoxide in MeOH. The influence of the reaction medium on the outcome of the annulation reaction in the case of one 2-pentyn-1,6-dione (heteroannulation vs. carbocyclization) is also shown.
Synthesis of pyrylium salts by the action of the trityl cation on penta-2,4-dienones. Experimental study and mechanism
Barry-Kone, N.,Fossey, J.,Loupy, A.,Sib, S. F.,Simalty, M.,Sorba, J.
, p. 218 - 222 (2007/10/02)
The mechanism of the formation of pyrylium perchlorate or triflate salts has been investigated by reacting the trityl cation with several penta-2,4-dienones.The influence of various structural factors and the nature of the electrophilic reactant was studi
