Download e-book for kindle: 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 workforce on the double bond / Georgii Furin
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The reaction proceeded efﬁciently in 1 min and the ester linkage survived under the reaction conditions (Scheme 73) (98TL5631). Another efﬁcient method for the t-Boc deprotection of nitrogen atoms has been developed by coupling 278 with silica gel and MWI for 1–3 min to give the pyrrolidin-2-ones 279 in 91–96% yield (Scheme 73) (98SL147). 5 min. The acid 282 was produced as a minor by-product (3%) (Scheme 74) (98TL8437). 5. Indoles and Carbazoles Domino hydroamination-cyclization of 2-chlorostyrene (283) with aniline in the presence of potassium tert-butoxide in 1:1:2 ratio under MWI in a domestic MW oven gave N-phenylindoline (284).
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. Nitrile oxides 373 can be readily generated under MWI from the aromatic aldoximes 370 by halogenation and dehydrohalogenation with NCS/Al2O3 or by dehydrohalogenation of chlorohydroxamic acid 371 by Al2O3.
MW thermolysis of a quinoline solution of 317 in a sealed tube in the presence of copper chromite (5%) gave a low yield (3%) of indole whereas CuCl proved to be an efﬁcient catalyst, giving 83% of indole (318, R2 ¼ H) within only 12 min of thermolysis. However, using the copper(II) salt of 317 in quinoline led to a 4% yield of the decarboxylated indole, but thermolysis using copper powder as a catalyst produced a 94% yield of indole (93JOC5558). The dry condensation of oxindole (319) with carbonyl compounds supported on KF/alumina without solvent under MWI occurred without difﬁculty.
Advances in Heterocyclic Chemistry by Alan R. Katritzky