By Alan R. Katritzky
This quantity within the sequence summarizes the various 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 - finished overview of those hugely vital intermediates for the education of a wide selection of traditional items. The e-book explains how 1,2,4-Triazolo [1,5-a] pyrimidines are of specific significance in images with different major software in prescribed drugs and agrochemicals. It additionally stories tetramic acids, an importantgroup of traditional items exhibiting signifcant organic task, in addition to a few chemistry.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 57
Extension of this reaction to methanesulfonyl chloride permitted preparation of open-chain derivatives 109 in 88-90% yield, which in turn cyclized in the presence of lithium diisopropylamide to 2H-1,2-thiazines 110 in 82-92% yield (89TL4705). Earlier work by the Komatsu-Ohshiro group showed that the reaction of simple 1-azadienes JOSE BARLUENGA AND MIGUEL TOMAS 24 8' LDA THF -78°C + 25°C - R'NHz R39 [Sec. B R3 R4 I 0 H 108 107 NHR' R4 A N 'H 2 LDA N-SO2 H/ - R"H2 109 I H 110 SCHEME 27 with enolates of substituted acetates gives rise to mixtures of 2-pyridones and isomeric dihydro-Zpyridones (8 1TL3769).
DMAD Toluene -20+25"C R4 N / c ~ ~ RM Z = R 3~= H * 117 2 123 'Co2Me 5* DMAD : Me02C-C=Cc-C@Me 125 SCHEME 3I substituted 1,5-diazocine-2(1H)-ones 124, and their aqueous hydrolysis gave quantitatively new 1,2-dihydropyrimidines 125 as well. In the case of starting with azadienes 2 having R2 = R3 = H, the formation of corresponding diazagermocines 123 takes place at -20°C and were not isolated, but either allowed to warm to room temperature to afford 117 or hydrolyzed to pyrimidines 125 (R2 = R3 = H).
Acid hydrolysis of them resulted in their aromatization to yield 2-pyrindine (n = 13 and isoquinoline (n = 2) derivatives 214. Imines derived from aniline and glyoxylic acid esters can be regarded as electron-poor 2-azadienes, in which an aromatic carbon-carbon double bond takes part of the diene system. In this context, Prato and Scorrano et al. were able to achieve the [4 + 21 cycloaddition of ethyl N-phenyl glyoxylate imines with dihydrofuran and indene leading to hexahydrofuro[3,2-c]- and tetrahydro-7H-indeno[2,l-c]quinolines,respectively, in moderate to good yields (88JHC 183 1).
Advances in Heterocyclic Chemistry, Vol. 57 by Alan R. Katritzky