By Alan R. Katritzky
This quantity within the sequence summarizes the numerous tools of the synthesis of heterocycles from azadienes with sections overlaying 1-azadienes, 2-azadienes, and 1,3-diazadienes. It covers the piperazine-2,5-diones and comparable lactim ethers - complete assessment of those hugely very important intermediates for the training of a large choice of average items. The publication explains how 1,2,4-Triazolo [1,5-a] pyrimidines are of specific significance in images with different major program in prescribed drugs and agrochemicals. It additionally studies tetramic acids, an importantgroup of traditional items displaying signifcant organic task, in addition to a few chemistry.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 57
Representative examples by Saito and Motoki (92CC22)and Molina (91TL5379) leading to quinolines 173 and pyrido[2,3,4-de]quinazolines 177, respectively, are shown in Scheme 41. - R'N=C=O 25"C+ 170°C I ii Nx R1 *'"'" q7c02 II ii 174 P I1 175 /N N II - \ 'yN\ NHR' Rl il XH X 17 7 (X = NR2, 43-50 %) 176 (X = CR2R3: 69-70 %) SCHEME 41 Sec. B] SYNTHESIS OF HETEROCYCLES FROM AZADIENES 37 were prepared in more than 81% yield from iminophosphoranes 170 and aryl isocyanates, underwent electrocyclization at 140°C to produce 2aminoquinolines 173 via prototropic aromatization of 172.
The stereochemistry of the resulting adducts is in agreement with an endo transition state in the case of dienophiles lacking a cis alkyl substituent at the p-carbon (n-butyl vinyl ether, benzyl vinyl ether, and 1-morpholino cyclopentene), whereas an exo transition state was involved when dihydropyrane or cis-propenyl benzyl ether were used. Finally, the authors reported that cyclohexene and dimethyl acetylenedicarboxylate failed to react with these unactivated 2-azadienes.
C02Et. SO2Me SCHEME 51 decisively the cycloaddition; in fact, using open-chain bis-dienophiles did result in the formation of alkenyl pyridines. 1,4-Bis(dimethyIamino)-2-azabutadienes226 have been reported by Biere et al. 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).
Advances in Heterocyclic Chemistry, Vol. 57 by Alan R. Katritzky