Heterocycles by Transition Metals Catalyzed Intramolecular Cyclization of Acetylene Compounds

S.A. Vizer, K.B. Yerzhanov, E.C. Dedeshko

Institute of Chemical Sciences MES Republic Kazakhstan, Sh. Walikhanov str. 106, Almaty, 480100, Kazakhstan

Abstract

Review shows the new strategies in the synthesis of heterocycles, having nitrogen, oxygen and sulfur atoms, via transition metals catalyzed intramolecular cyclization of acetylenic compounds on the data published at the last 30 years. Unsaturated heterocyclic compounds (pyrrols and pyrrolines, furans, dihydrofurans and benzofurans, indoles and isoindoles, isoquinolines and isoquinolinones, aurons, isocoumarins and oxazolinones, lactams and lactones with various substitutes in heterocycles) are formed by transition metals (Pdo/C), those salts [PdCl2, Pd(OAc)2, HgCl2, Hg(OAc)2, Hg(OCOCF3)2, AuCl3.2H2O, NaAuCl4.2H2O, CuI, CuCl], oxides (HgO) and complexes [Pd(OAc)2(PPh3)2, Pd(PPh3)4, PdCl2(MeCN)2, Pd(OAc)2/TPPTS (sodium triphenylphosphyntrisulfonat)] catalyzed intramolecular cyclizations of acetylenic amines, amides, ethers, alcohols, acids, ketones and β-diketones. More complex heteropolycyclic systems typical for natural alkaloids can to obtain similar. Proposed mechanisms of pyrrols, isoquinolines, isoindoles and indoles, benzofurans and isocoumarins, thiazolopyrimidinones formation are considered.