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2005
Multi-membered O,N,S-heterocycles
R 0692
Novel Pyrrolo[1,2-a][3.1.6]benzothiadiazocine Ring Synthesis. Unusual
Type Rearrangement of 1-{[1-(2-Nitrophenyl)-1H-pyrrol-2-yl]sul02- 167 Truce—Smiles
fonyl (or sulfinyl)}acetone. — Treatment of nitrophenyl compounds of type (I) with
Zn, NH4Cl does not yield expected thiadiazepines but hydroxylamines like (III) and
amines such as (II). In the presence of NaOH with or without Zn, (Ie) and (If) undergo
unusual Truce—Smiles rearrangement to the nitro compounds (V). Interestingly,
reduction of the nitro group does not occur. Under these conditions (Ia) and (Ib) lead
to complex mixtures whose components can not be identified. Reaction of (Ia), (Ib),
and (Id) with NaBH4/Pd-C results in formation of the novel thiadiazocines (VI) and
(VII). — (KIMBARIS, A.; COBB, J.; TSAKONAS, G.; VARVOUNIS*, G.;
Tetrahedron 60 (2004) 40, 8807-8815; Dep. Chem., Univ. Ioannina,
GR-45110 Ioannina, Greece; Eng.) — Jannicke
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