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 - finished overview of those hugely vital intermediates for the practise of a large choice of traditional items. The e-book explains how 1,2,4-Triazolo [1,5-a] pyrimidines are of specific value in images with different major software in prescribed drugs and agrochemicals. It additionally studies tetramic acids, an importantgroup of average items displaying signifcant organic job, in addition to a few chemistry.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 57
The carbon-oxygen double bond also proved to participate in this reaction, forming the 1,3-oxazine ring; in fact, stirring at room temperature a tetrahydrofuran solution of 2 and esters of glyoxylic acid followed by aqueous work-up resulted in a clean conversion into 2H-1,3-oxazines 106 in excellent yields (92UP1). It should be noted that 2 condensed with ordinary 99 98 R = Me,CHzPh SCHEME 25 Sec. ILB] 23 SYNTHESIS OF HETEROCYCLES FROM AZADIENES I R'CN or DMAD 25-1WC R3= Me - '2 ml 60°C R4 H ' 2 Y 104 (R3 = Me: X = NR'; 103 Y = S) 105 (R3 = H x = Y = S) R2 25OC - R'NH2 106 DMAD : Me@C-C=CC-CO2Me SCHEME 26 aldehydes and, occasionally, with heterocumulenes in a [5 + 11 manner (Section 11,B,2).
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.
We have described (88TL4855) a simple synthesis of pyridin-2-ones by a two-step annulation of 2 with aliphatic acid chlorides (Scheme 27). The acylation of aminoazadienes 2 in pyridine furnished 4-amidoyl-lazabutadienes 107 in high yields (85JOC802); lithium diisopropylamidecatalyzed aldol-type cyclization of 107 afforded pyridin-2-ones 108 in 83-94% yield. 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).
Advances in Heterocyclic Chemistry, Vol. 57 by Alan R. Katritzky