By Alan R. Katritzky
This quantity within the sequence summarizes the various equipment 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 comparable lactim ethers - complete evaluate of those hugely very important intermediates for the education of a wide selection of ordinary items. The ebook explains how 1,2,4-Triazolo [1,5-a] pyrimidines are of specific significance in images with different major software in prescription drugs and agrochemicals. It additionally studies tetramic acids, an importantgroup of normal items exhibiting signifcant organic job, in addition to a few chemistry.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 57
Have been able to cyclize systems 250, in which the dienophilic partner can be substituted with either electron-donating or -acceptor groups, to give a-carbolines 252 in 31-55% yield; the participation of one aromatic carbon-carbon double bond in the cycloaddition process was also shown to occur since diary1 carbodiimides 253 furnished, under the same reaction conditions, quinindolines 255 in 28-54% yield. The Japanese group also obtained 252 in 33-45% yield by heating 251 followed by oxidation; these authors were able to increase the scope of this cycloaddition to furyl- and thienyl-substituted carbodiimides 254, which gave 256 in 33-55% yield under the same reaction conditions.
The reaction of 2-azadienes 232 with enolates derived R‘ PhZO 235-250°C H’ N* *q0 0 232 238 OH I 240 SCHEME 54 239 (47-92%) R3 = OEt, Me Sec. B] 49 SYNTHESIS OF HETEROCYCLES FROM AZADIENES from diethyl malonate or ethyl acetylacetate at room temperature furnished the addition products 238, which in turn were cyclized to pyridones 239 upon heating in phenyl ether (86JOC1374). Following this methodology, a short and convergent total synthesis of the fungal biochrome tenellin 240 was developed (89JOC5852).
SIX-MEMBERED RINGS 1. From [6 + 01 Fragments Electrocyclic ring closure reactions of vinyl or aryl 2-azadienes (azatrienes) involving six electrons have been reported to occur at moderate temperatures and, in this respect, several pyridine syntheses have been described. While preparing 2-azadienes, Corriu et al. and our group have observed that electrocyclic ring closure takes place in some instances (Scheme 38). Corriu (82TL3257) obtained pyridine 155 in 67% yield by reaction of N,N-bis(trimethylsily1)enamines153 and chalcone, probably through intermediate 154.
Advances in Heterocyclic Chemistry, Vol. 57 by Alan R. Katritzky