By Alan R. Katritzky
This quantity within the sequence summarizes the numerous 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 comparable lactim ethers - entire assessment of those hugely very important intermediates for the guidance of a large choice of average items. The booklet 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 stories tetramic acids, an importantgroup of ordinary items exhibiting signifcant organic task, in addition to a few chemistry.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 57
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). In the same way, double nucleophilic displacement on dichlorophosphines allowed the first-time preparation of the 1,4-azaphosphorine ring; stirring at room temperature a mixture of 2-azadiene 139 and dichlorophenyl- or trichlorophosphine in hexane followed by aqueous work-up resulted in the formation of 1,Cdihydro- Sec.
C] SYNTHESIS OF HETEROCYCLES FROM AZADIENES 27 from azadienes 2 having R2 and R3 other than hydrogen toward dimethyl acetylenedicarboxylic acid (Scheme 30). When azadienes 2 (R2 = Ph; R3 = Me) and dichlorodiphenyl silane were stirred in toluene at room temperature and then heated at 60°C with dimethyl acetylenedicarboxylic acid, eight-membered heterocycles 121 were isolated in 60-71% yield. All attempts to desilylate compounds 121 preserving the ring structure failed; thus, the protodesilylation reaction induced by trifluoroacetic acid resulted in the simultaneous ring contraction to pyridines 122 in quantitative yield.
Using 2-azadienes 139, we have prepared a number of A3thiazolines 140 in yields higher than 81% by heating a mixture of azadiene and elemental sulfur without solvent (170°C) or in toluene (SOOC) (92T9745). Moreover, Komatsu et al. isolated thiazoles 142 on reaction of simple 2-azadienes 141 with sulfur dichloride (83PS119) (Scheme 35). However, vinyl isocyanates have been nicely demonstrated by the Rigby group to be particularly useful intermediates in synthesis of pyrroli- . 4 R 1 KCN 'YcN MeOH X=C@Me X X 137 136 R2 = Ph R3 = Me R2-R3 =(CH2)4 R4 = H, Me R5 = Ph.
Advances in Heterocyclic Chemistry, Vol. 57 by Alan R. Katritzky