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 staff on the double bond / Georgii Furin
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Additional info for Advances in Heterocyclic Chemistry
The reaction of indoles 304 with Meldrum’s acid (305) and paraformaldehyde in acetonitrile in the presence of D,L-proline catalyst was investigated both by conventional heating and MW irradiation. In all cases, adducts 307 were formed along with their hydroxymethylated derivatives 306 in good yields; the MW irradiation reduced the reaction time and gave cleaner reaction mixtures (Scheme 79) (99S254). When the product 306 (R1 ¼ Br) in a mixture of acetonitrile and triethylamine was exposed to MWI at 85 1C for 60 min, it afforded 307 (R1 ¼ Br) in quantitative yield (Scheme 79).
Thus, several fulleropyrrolidines 243 were prepared in 15–37% yields by irradiating a solution of C60, aromatic aldehyde and glycine in dry o-dichlorobenzene (ODCB) in a focused MW reactor. The redox potentials of the prepared compounds were determined by cyclic voltammetry (97T2599). Alkylation of 243 has not been described, probably because of the low reactivity of these compounds. H. EL ASHRY ET AL. 36 R 3 R O O R N N R 1 R 2 O O MW, 30 min 3 3 - H 2O R R 1 R N N HO HO R 1 R 2 3 R N H 3 2 R 1 3 3 O HO R N N R 1 R 2 3 O -R H R O R N O N N OH O 241 O R [Sec.
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.
Advances in Heterocyclic Chemistry by Alan R. Katritzky