By Alan R. Katritzky
This quantity within the sequence summarizes the numerous tools of the synthesis of heterocycles from azadienes with sections protecting 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 coaching of a wide selection of average items. The booklet 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 average items exhibiting signifcant organic job, in addition to a few chemistry.
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 57
Pyridone 242 (X = 0) was the major isomer in the case of isocyanates, whereas the [2 + 21 cycloaddition leading to 244 (X = S) was the preferred pathway for isothiocyanates. Giffard and Cousseau reported that vinyl isocyanates cycloadd to tetracyanoethylene in a [4 + 21 fashion leading to 3,4-dihydropyridine-2( lH)-thiones [85JCR(S)300]. Previous examples regarding cycloaddtion reactions of vinyl isocyanates and 4sothiocyanates with enamines and ynamines have been published [70AG(E)159, 70T2161, 78JOC402].
CN Y =CH,N 57-90 % X = CN. C a M e R4 = Me, (CH2)z-OH. (CH2)z-OMe. CHzPh R3 = Me. C q M e R5 = Me, Ph, OH, NH2 SCHEME 42 leads to N-trimethylsilyldivinylamines (86CC361). Therefore, one could expect azadienes 139 to participate in [5 + I ] heteroannulations (Schemes 44 and 45). The carbonylation reaction leading to 4(1H)-pyridones 188 was accomplished by room temperature treatment of 139 with N , N ' carbonyldiimidazole in the presence of boron trifluoride etherate [90TL(31)3793;91JOC67511(Scheme 44).
The preparation of 2-azadienes 212 with two appended methoxycarbonyl groups was achieved, in a multigram scale and in nearly quantitative yield, by the insertion reaction of N - trimethylsilyl imines 210 into the carbon-carbon triple bond of dimethyl acetylenedicarboxylate to give 211 followed by protodesilylation with CsF/MeOH. Azadienes 212 underwent at room temperature inverse-electron demand [4 + 21 cycloaddition with cyclic enamines to give exclusively em-cycloadducts 213 in 82-95% yield. Acid hydrolysis of them resulted in their aromatization to yield 2-pyrindine (n = 13 and isoquinoline (n = 2) derivatives 214.