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2005
Multi-membered N-heterocycles
R 0690
Substituted and Fused Spiro[benzo-2-azepine-3,1'-cyclohexanes]. — Cyclic nitro(I) is rearranged into lactam (II), which is used for the synthesis of fused triazoles
20- 163 ne
(VII) and (X) and fused tetrazole (XI). Condensation of thioimidate (V) with benzohydrazide (VI) gives rise to the formation of triazole (VII), while condensation of (V) with
isonicotinohydrazide (VIII) under the same conditions yields (IX), which exists in an
iminol form. Ring closure into triazole (X) is achieved by heating in polyphosphoric
acid. Successive treatment of (II) with thionyl chloride and sodium azide provides tetrazole (XI). — (VARLAMOV, A. V.; GRUDININ, D. G.; CHERNYSHEV, A. I.;
LEVOV, A. N.; LOBANOV, I. Y.; BORISOV, R. S.; ZUBKOV*, F. I.; Russ. Chem.
Bull. 53 (2004) 8, 1711-1716; Dep. Org. Chem., People's Friendship Univ., Moscow
117419, Russia; Eng.) — H. Hoennerscheid
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