By Alan R. Katritzky
The most recent quantity within the Advances in Heterocyclic Chemistry sequence.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 56
Scope and Organization . . . . . . . 11. Rearrangements Involving the Pivotal Nit A. Rearrangements Involving Cleavage of an 0-N Bond.. . . . . . . . I . Rearrangements Involving a Side-Chain CNO.. . . . . . . . . . 2. Rearrangements Involving a Side-Chain CNN. . . . . . . . . . 3. Rearrangements Involving a Side-Chain NCO . . . . . . . . . . 4. Rearrangements Involving a Side-Chain CCO . . . . . . .
Leigh, J. Heterocycl. Chem. 26, 1619 (1989). A. R. Butler, D. Lloyd, H. McNab, D. R. Marshall, and K. S. Tucker, Liebigs Ann. , 133 (1989). E . W. Della, G. M. Elsey, and G. Skouroumounis, Ausr. J. Chem. 43, 1231 (1990). G. Ferguson, M. Parvez, D. Lloyd, H. McNab, and D. R. Marshall, Acta Crysrallogr.. Sect C C46, 1248 (1990). D. Lloyd, G. Ferguson, and B. L. , Sect. C C47, 1290 (1991). Ferguson, D. Lloyd, H. McNab, D. R. Marshall, B. L. Ruhl, and T. S. Perkin 2, 1563 (1991). 83JOU 1388 83LA1209 83LA1230 83ZOR1541 84AX(C)1740 84LA649 84M11 85JHC405 85LA1969 85S339 86LA1368 86LA 1380 86LA1387 86M11 87JCS(P2)I 129 87MI 1 88CCC 1529 88MI 1 89JHC1619 89LA133 90AJC 123I 90AX(C)1248 91AX(C)I290 48 UP1 u P2 UP3 UP4 UP5 DOUGLAS LLOYD AND HAMISH McNAB A.
The first step involves the formation of a ally1 radical. - Sec. , the 5- and 7-positions. If, however, there are substituents at the 5,7-positions they inhibit or retard further reactions, and the initial reduction is reversible: D++D' slow , products (D=dihydrodiazepine) In the case of 5,7-unsubstituted compounds, reduction is followed immediately by a chemical reaction, preventing the setting-up of an equilibrium between the cation and the radical, and causing the reduction to be effectively irreversible: D + ~ D * , products (D=dihydrodiazepine) Preparative studies on the 5,7-diphenyl derivative suggest that reduction is followed by a disproportionation process leading to the formation of the dihydrodiazepine base and a tetrahydrodiazepine [UP4; 8OJCS(P2)668].