Advances in Heterocyclic Chemistry, Vol. 57 by Alan R. Katritzky

By Alan R. Katritzky

This quantity within the sequence summarizes the numerous tools of the synthesis of heterocycles from azadienes with sections masking 1-azadienes, 2-azadienes, and 1,3-diazadienes. It covers the piperazine-2,5-diones and similar lactim ethers - complete evaluation of those hugely vital intermediates for the coaching of a large choice of typical items. The publication explains how 1,2,4-Triazolo [1,5-a] pyrimidines are of specific value in images with different major program in prescribed drugs and agrochemicals. It additionally stories tetramic acids, an importantgroup of common items displaying signifcant organic task, in addition to a few chemistry.

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Sec. B] 41 SYNTHESIS OF HETEROCYCLES FROM AZADIENES - HCI 191 192 (55-62 %) - H2 R4 = Ph. C-C~HI1 R2 = Me, Et, Pr. 3-butenyl 193 195 196 194 (47-92 %) 197 19 8 (67-88 %Ib) R3=Ar,H SCHEME 45 Further work has been carried out by Ghosez (88TL3799, 88TL4573, 88TL6115; 89TL5887, 89TL5891) and others (79CL187; 87CB657, 87HCA1255; 88TL4401). Moreover, the cycloaddition reaction of 2azadiene 202 (Scheme 47) has been employed as the key step in the synthesis of alkaloid amphimedine 204 reported by Echavarren and Stille (88JA4051) and of marine antibiotic mimosamycin 205 carried out by McKillop and Brown (87SC657).

To undergo acid-catalyzed heterocyclization with indoles and pyrroles (Scheme 52). P-Carboline derivatives 228 were synthesized in 41-84% yield by refluxing a mixture of azadienes 226, indole derivatives, and acetic acid; dehydrotryptophan derivatives 227 could be isolated under mild reaction conditions (86LA 1749). Indolo[ 1,2-c]pyrimidine 229 was formed in 30% yield if 3-methylindole was used (87LA491). When this cyclization was extended to pyrroles, the authors found that, in some cases, mixtures of pyrrolo[ 1,2-c]pyrimidines 230 and pyrrolo[3,2-c]pyridines 231 were obtained, though in all cases the reaction initiates through the C-2 of the pyrrole.

C The preparation of seven-membered heterocycles was accomplished by starting from azadienes 2 with no substituents at both C,- and CB-enamine carbon atoms (R2 = R3 = H) (Scheme 29). Sequential treatment of those azadienes 2 with dichlorodiphenylsilane or -germanium followed by reaction of the resulting solution with DMAD at 60 or 25°C (for silicon or germanium derivatives, respectively) gave new furo[2,3-6][ 1,4]diazepines 116 and 117; either protodesilylation or protodegermylation to 118 (40-90% yield from 2) was carried out by stirring at room temperature a dichloromethane solution of trifluoroacetic acid and 116 or 117.

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