By Alan R. Katritzky
Content material: Microwave irradiation for accelerating natural reactions. half I: Three-, 4- and 5-membered heterocycles / E S H El Ashry, E Ramadan, AA Kassem, M Hagar -- Organometallic complexes of the n²(N, C)-coordinated derivatives of pyridine / Alexander Sadimenko -- Annulated heterocyclo-purines II: fused six- and more-membered heterocyclo-purinediones, -purinones and -purineimines / Alfonz Rybar -- Flourine-containing heterocycles. half II: Synthesis of perfluoroalkyl heterocycles utilizing perfluoroolefins containing a reactive team on the double bond / Georgii Furin
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2 min. A conventional method took 21–36 h to give 334 in 87–90% yield (Scheme 85) (94JOC3408). H. EL ASHRY ET AL. 50 [Sec. 2 min O 333 O 334 Scheme 85 X R O R Pd(OAc)2, DPPP Et3 N, DMSO MW, 5-7 min O O O HO 336 Pd(OAc)2, DPPP Et3 N, DMSO MW, 7 min TfO O 337 335 O O 338 Scheme 86 A mild chemo- and regioselective procedure for the direct synthesis of 2-alkene-2methyl-1,3-dioxolanes 337 (45–89%) uses Heck vinylation of 2-hydroxyethyl vinyl ether 336 with a vinyl triflate or bromide in the presence of palladium acetate catalyst, 1,3-bis(diphenylphosphino)propane (DPPP) a chelating ligand and triethylamine by ﬂash heating under MWI (00JOC4537).
A disk made of Teﬂon was designed to hold 28 vials in the highest irradiation area of a domestic MW oven. 5 min at 550 W to give 28 N-aryl phthalimides in 34–97% yields (02SL343). The general method for the synthesis of N-aryl phthalimides needed a long heating under reﬂux (59JOC388). However, a mixture of phthalic anhydride 115 and aromatic amine in an open container in a MW oven and irradiated for 2–10 min gave N-aryl phthalimides in 91–95% yields (02SC927). A preparation of N-alkyl imides under microwave assistance on polymer support in the solid state has been developed.
EL ASHRY ET AL. 40 [Sec. A Merriﬁeld resin, treated with phthalic anhydride and TaCl5/SiO2, and subjected to MWI for 5 min to furnish polymer bound imide 261 whose cleavage from resin by treatment with triﬂuoroacetic acid in CH2Cl2 gave 262 in 65% yield. Maleic anhydride and succinic anhydride also gave the respective imides in 65 and 60% yields (Scheme 68). Similar results were observed by the use of polymer-supported alanine with phthalic anhydride, maleic anhydride or succinic anhydride (99SL1597).