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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Extra info for Advances in Heterocyclic Chemistry
5 min, 3,3,6-trimethyl-3,3a,4,5,6,7-hexahydro-2,1-benzisoxazole 369 was obtained in 78% yield (Scheme 93) (94JOC3408). H. EL ASHRY ET AL. 5 min [Sec. 5 min O N 368 369 Scheme 93 YHC=CHZ R-CH=N-OH 370 Cl R-C=N-OH 371 MeO2CCH2NO2 NCS, Al2O3 MW, 10 min O H Y N H R C N O N ZC CY O H Y N O Z H 374b R H N O + R H 375a R C N O H 375a R N R O + Y 372 O N R + Z H 374a Al2O3 MW, 10-30 min - H2O MW, 30 min R Z 376a 373 Y Z 376b Scheme 94 The 1,3-dipolar cycloaddition of a nitrile oxide with a dipolarophile to give isoxazoles or isoxazolines is readily achieved in the presence of catalytic amounts of PTSA, under MWI.
However, the cleavage of sulfonamides 316 was carried out using KF/Al2O3 under MWI within 5–6 min to give indoles 318 in 76–80% yields. The cleavage of the N-Ts group of carbazole under similar condition by MWI took place within 6 min to give carbazole in 78% yield (Scheme 81) (99SL1745). Indole-2-carboxylic acid (317) was quantitatively decarboxylated to indole after 20 min at 255 1C in water in a MW batch reactor (MBR). 2-Carbethoxyindole (309) underwent low conversion into indole under these conditions.
Dramatic acceleration in the rate of dehydration due to MW heating was established. Conventional heating of aldoximes with the inorganic catalyst formed nitriles only to a minor extent and longer reaction times are required to achieve higher yields. A very quick and simple dehydration of thiophene 2-aldoxime (212) on the surface of a H2SO4/SiO2 solid support catalyst was promoted under MWI for 5 min to afford 2-cyanothiophene (213) in 64% yield (97SC1327). Aldoxime 212 can be rapidly converted into nitrile 213 in 88% yield with DBU under MWI within 2 min (Scheme 55).
Advances in Heterocyclic Chemistry by Alan R. Katritzky