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 workforce on the double bond / Georgii Furin
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The yield was higher than that of a conventional heating method with a much shorter reaction time (02MI4). (Phthalocyaninato)bis(chloro)silicon 246 was prepared in high yield (91%) by MW heating of diiminoisoindolene and silicon tetrachloride in quinoline. The reaction was carried out in a modiﬁed MW ashing furnace and required 5 min compared to 30 min with thermal heating (Scheme 64) (01MI3). Sec. A] 37 MICROWAVE IRRADIATION O 4 + O Urea + M N MW NH NH + SiCl4 N N N M N 4-7 m in O 4 2+ N N lin e in o n u Q mi ,5 W M N 245 M = Cu, Co, Ni, Fe 246 M = SiCl2 NH Scheme 64 Ar + N Zeolite Ar CHO MW, 3-5 min H N Ar Ar N H H N N Ar 248 247 Scheme 65 The MW-assisted cyclocondensation of pyrrole (247) and benzaldehyde adsorbed on a solid acidic support, afforded tetraphenyl porphyrin (248) within 10 min.
B-Aminoalcohols with varied substituents on the chain carbons are excellent precursors for the synthesis of oxazoles and oxazolidenes via the insertion of one carbon atom. Various one carbon inserting agents have been used in this regard as cyclizing agents. The condensation between aminoalcohols 399 such as ephedrine and an aldehyde under solvent-free conditions using a focused MW reactor gave 1,3-oxazolidines 400 in excellent yields and diastereoselectivities (Scheme 101) (01MI4). The synthesis of oxazolines 401 was achieved by the reaction of imino ether hydrochlorides 402 with 399 in the presence of KF supported on alumina; the reaction was carried out in an open vessel.
EL ASHRY ET AL. 56 [Sec. B R 1 R -CH=CH 2 MW, 6-30 min R N O Ph 387 Ph O Ph O 389 MW, 10 min R 1 O 388 N Ph Ph Ph O O R H N O Ph 390 Scheme 97 The isoxazoles can also be prepared via the rearrangement and subsequent cycloaddition of 3,4-dibenzoyl furoxan 385 with dimethyl acetylenedicarboxylate under MWI for 12 min, via benzoylnitrile oxide to give 386 in 60% yields (Scheme 96). Increasing the reaction time gave no significant improvement in yields, but decomposition of the product occurred. Several structurally varied dipolarophiles including phenyl acetylene, styrene, phenyl styrene, N-methylmaleimide and 4-phenyl-3-butyn2-one underwent clean and remarkably fast cycloaddition with diaroyl furoxans under this procedure (98SC2415).