By Alan R. Katritzky
This quantity within the sequence summarizes the various tools 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 similar lactim ethers - finished evaluation of those hugely very important intermediates for the coaching of a large choice of normal items. The ebook explains how 1,2,4-Triazolo [1,5-a] pyrimidines are of specific significance in images with different major program in prescription drugs and agrochemicals. It additionally reports 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
1 Y P h Ph N H20 hv If HfyPh Ph 160 159 H30' 162 (51-64%) SCHEME 39 N h* OCOPh / H' Ph Ph 161 Sec. B] 35 SYNTHESIS OF HETEROCYCLES FROM AZADIENES R2 =-N 3 R3 = CQEt, COPh, COMe 165 X CO,Et ArHN+- / CN EtO or / EtOH JPTSOH / c& - NYNHz or HCI / Dioxane Ph 166 A~HN,&Y \ NYN Ph 167 (X = CN;Y = OH) 168 (X = C02Et: Y = NH2) 169 (X = CQEt; Y = Cl) SCHEME 40 50-70% yield substituted pyrimidines 167, 168, and 169 by treatment of azadiene 166 with ethoxide ion, acid, and hydrogen chloride, respectively (84TL1291).
Following this strategy, the authors were able to achieve the total synthesis of piperidine alkaloid (+)-sedridine 90 in a few steps (Scheme 22); the process implies the diastereoselective intramolecular Diels-Alder reaction of the 1-azadiene derived from acrolein, lithium hexamethyldisilazane, and the homoallyl chlorocarbonate to give k& FVP 0 OAc 80 81 82 0 83 84 SCHEME 21 20 JOSE BARLUENGA AND MIGUEL TOMAS [Sec. - H2. - KOH 0 89 90 SCHEME 22 cycloadduct 89 in 30% yield, followed by reduction of the carbon-carbon double bond and cleavage of the urethane ring (91TL4371).
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. The 230 :231 ratios reported are compiled at the bottom of Scheme 52 (87LA491). Unexpectedly, Grieco discovered that immonium ions derived from aryl amines and aldehydes do not function as heterodienophiles toward cyclopentadiene, as was found in the case of simple immonium ions, but rather they acted as 2-azadienes leading to a novel synthesis of tetrahydroquinolines (88TL5855).