Advances in Heterocyclic Chemistry by Alan R. Katritzky

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 crew on the double bond / Georgii Furin

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Advances in Heterocyclic Chemistry

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.

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Similar results were observed by the use of polymer-supported alanine with phthalic anhydride, maleic anhydride or succinic anhydride (99SL1597). Several strategies have been employed for the synthesis of thalidomide 265; a drug achieving great therapeutic importance in the treatment of several diseases. It was synthesized in 91% yield by cyclization of N-phthaloylglutamine (99MI5). However, irradiation of L-glutamine 264 in the presence of phthalic acid 263 in a domestic MW oven gave pyroglutamic acid 266 as the only product.

For instance, maleic anhydride 113 on treatment with benzylamine yielded N-benzyl maleimide in 82% yield. Similar results were observed with aniline and R(+)-a-methylbenzylamine; otherwise less reactive succinic anhydride was converted into the corresponding succinimides in 75–80% yields (97TL8089). 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).

The a; b-unsaturated acid 218 was formed in almost quantitative yield when a mixture of aldehyde 216 and malonic acid together with ammonium acetate was subjected to MWI for 3 min. The reaction was performed in an open Erlenmeyer flask in the absence of solvent (Scheme 56) (98SC3811). Reductive coupling of thiophene 2-aldehyde (216) with TMS-Cl on montmorillonite K10 clay under MWI, in a similar manner to that of furaldehyde, gave the silylated pinacol coupling product 219 in 80% yield (Scheme 56) (98SC2017).

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