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Reactions of 3-Hydrazino-1,2,4-triazino[5,6-b]indole with alfa, beta-unsaturated ketones, esters and nitriles

Youssef A. S. A.

Bulletin of the Polish Academy of Sciences. Chemistry

2001

Vol. 49, No. 1

9-16

3-Hydrazino-l,2,4-triazino[5,6-b]indole (1) reacted with l-aryl-3-phenylprop- 2-yn-l-ones (Ila-c) to give 3-1'-(5'-aryl-3'-phenyl)pyrazolyl] 1,2,4-triazino[5,6-b]indoles (Illa-c). o;-(p-Chlorobenzoyl) acephenone-N-3(l,2,4-triazino[5,6-b]indole) hydrazone (IV) was isolated in case of (lib) only. On the other hand, methyl p-chlorophenyl prop-2-ynoate (lid) gave 3-[1'-(3'-p-chlorophenyl-5'-hydroxy) pyrazolyl] l,2,4-triazino[5,6-b]indo-le (Hid). (I) reacted with diethyl but-2-yndioate (VI) to give 3-[1'-(3'-carboethoxy-4'-hydro-5'-oxo) pyrazolyl] l,2,4-triazino[5,6-b]indole (VII) and diethyl oxaloacetate- N- 3-(1,2,4-triazino[5,6-b]indole) hydrazone (VIII). Similar treatment of (I) with 2-cyano-(IXa) or 2-cyano-3-methyl- (IXb) cinnamonitriles afforded 3-[2'-(4'-phenylmethylene-3',5'-dioxo-4'-hydro) pyrazolyl] - (Xa) or 3-[2'-(4'-methyl phenylmethylene-3',5'-dioxo-4'-hydro) pyrazolyl]- (Xb) l,2,4-triazino[5,6-b] indoles, respectively.

Physical image vs. structure relation, 5 [1]. Multinuclear NMR structural study on some hydrazones of O,O-Dialkyl 1-Oxoalkanephosphonates

Nazarski R. B., Gralak D. K., Kudzin Z. H.

Bulletin of the Polish Academy of Sciences. Chemistry

2000

Vol. 48, No. 1

27-33

An unambiguous method for determination of the configuration of any single 0,0-dialkyl 1-oxoalkanephosphonate hydrazones based on H, C, P NMR data has been elaborated; the use of 1 JCp (P-C=N) couplings is the most fruitful. The 12C/13C isotope effects on the P chemical shifts of selected compounds have been measured. For primary hydrazones the E/Z isomerisation with stabilisation of their Z forms through an intramolecular H-bonding has been proven. In addition, for the latter stereoisomers small scalar couplings between H-bonded groups N-H.. .O=P have been found, JHP 2.4-3.4 Hz. The possibility of the across H-bridge transfer of spin-spin interactions in these forms is also discussed.

N-(E)-2-Stilbenyloxymethylenecarbonyl substituted hydrazones of ortho, meta and para hydroxybenzaldehydes

Wyrzykiewicz E., Błaszczyk A., Turowska-Tyrk I.

Bulletin of the Polish Academy of Sciences. Chemistry

2000

Vol. 48, No. 3

213-229

Twelve unknown N-(E)-2-stilbenyloxymethylenecarbonyl substituted hydra-zones of acetone and ortho, meta and para hydroxybenzaldehydes have been prepared. The N-substituted hydrazones occur as E geometrical isomers and cis/trans amide conformers (1) H NMR estimations). Crystal structures of N-(E)-2-stilbenyloxymethylenecarbonyl sub-stituted hydrazone of ortho hydroxy-benzaldehyde 10 and N-(E)-2/-(4/-chlorostilbenyloxy-methylenecarbonyl)-substituted hydrazone of meta hydroxybenzaldehyde 14 have been determined as E geometrical isomers and trans amide conformers with intra- (10) and intermolecular (14) hydrogen bonds.