By R. Ian Fryer
Quantity 50 of this sequence covers bicyclic diazepine compounds, discussing every one method, first so as of ring fusion after which based on expanding dimension of the fused ring (least measure of saturation first). The discussions of carbocyclic fused earrings precede these of heterocyclic fused earrings; besides the fact that, the place applicable, the benzene annelated ring approach is given choice over different fused ring structures. additionally, the nice quantity of fabric to be coated for the [e]-fused [1,4]- benzodiazepines has been prepared in 5 chapters for simple reference. The literature to 1985 has been surveyed for this quantity.
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Quantity 50 of this sequence covers bicyclic diazepine compounds, discussing every one process, first so as of ring fusion after which in line with expanding measurement of the fused ring (least measure of saturation first). The discussions of carbocyclic fused earrings precede these of heterocyclic fused jewelry; besides the fact that, the place acceptable, the benzene annelated ring approach is given choice over different fused ring structures.
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Additional info for Bicyclic Diazepines: Diazepines with an Additional Ring
Kurita and T ~ u c h i y a ” ~recorded the temperaturedependent proton-nmr spectra of compounds 81 (R = H, Me) and determined the energies of activation for the inversion of the seven-membered ring. 8 kcal/mol for the 5-methyl analog. The higher rigidity of the latter may be due to interaction of the 5-methyl group with the 6-proton. 3. 1. Also, isolated from this type of oxidation was the 3-vinyl indazole 106. Since 3H- 1,2-benzodiazepines are known to be susceptible to heat- and light-induced rearrangement^,^^ the diazepines 105 are believed to be intermediates (Eq.
Oxidation Reactions Treatment with lead tetraacetate of lH-l,2,-benzodiazepines 93, having an electron-withdrawing group such as methoxycarbonyl or cyano in the 3-position, resulted in the formation of the corresponding 5-acetoxy-SH-1,2benzodiazepines 94 in 68% yield. '" 21 1. 4. Acylation Reactions (95; R = H) with ethyl The reaction of 3-methyl-lH-l,2-benzodiazepine chloroformate in benzene at room temperature, gave the exo-methylene compound 96 and 2-methylquinoline N-ethoxycarbonylimide (97) as products.
The acetate could be removed in either acid or base and original starting material recovered (Eq. 91392 A reasonable mechanism was given, which proceeds via the photoinduced 174 175 36 Bicyclic 1,2-Diazepines formation of a diaziridine followed by ring expansion and tautomerisation to the 5H product through the 1H intermediate (Eq. 50). 3. 1. Synthesis As mentioned above, the tautomers 167 may be prepared by treatment of the lH-2,3-benzodiazepines 164 with base or heat. , condensation of a 1,5-diketone with hydrazine) has not been widely used and seems to be exemplified4' only by the synthesis of analogs of the 5H-2,3-benzodiazepine 180 by treatment of the 1,5-diketone 176 with hydrazine under acid catalysis (Eq.
Bicyclic Diazepines: Diazepines with an Additional Ring by R. Ian Fryer