Novel Synthesis of 3,4,4-Trisubstituted Thiadiazolines from 3,4-Diphenyl-1,2,5-Thiadiazole 1,1-Dioxide. Competition with the Intra-Molecular Aryl-Aryl Cyclization of 3,4-Diphenyl-1,2,5-Thiadiazole 1,1-Dioxide

María F.  Rozas; Oscar E.  Piro; Eduardo E.  Castellano; María V.  Mirífico; Enrique J.  Vasini

doi:10.1055/s-2002-35219

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Synthesis 2002(16): 2399-2403
DOI: 10.1055/s-2002-35219

PAPER

Novel Synthesis of 3,4,4-Trisubstituted Thiadiazolines from 3,4-Diphenyl-1,2,5-Thiadiazole 1,1-Dioxide. Competition with the Intra-Molecular Aryl-Aryl Cyclization of 3,4-Diphenyl-1,2,5-Thiadiazole 1,1-Dioxide

María F. Rozas^a, Oscar E. Piro^b, Eduardo. E. Castellano^c, María V. Mirífico^a,d, Enrique J. Vasini*^a
^a Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Facultad de Ciencias Exactas, Departamento de Química, Universidad Nacional de La Plata, C.C. 16, Suc. 4, (1900) La Plata, Argentina
Fax: +54(221)4254642; e-Mail: vasini@inifta.unlp.edu.ar;
^b Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata and IFLP (CONICET), C. C. 67, 1900 La Plata, Argentina
^c Instituto Física de São Carlos, Universidade de São Paulo, C.P. 369, 13560 São Carlos (SP), Brazil
^d Departamento de Ingeniería Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata , La Plata, Argentina

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Publication History

Received 19 March 2002
Publication Date:
04 November 2002 (online)

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Abstract

3,4-Diphenyl-1,2,5-thiadiazole 1,1-dioxide (1) reacted, in the presence of anhydrous aluminum trichloride, with aromatic nucleophiles possessing electron donor substituent groups to give novel (2a-e, Figure [1] ) 3,4,4-trisubstituted 1,2,5-thiadiazoline 1,1-dioxides in good yield. In the presence of aluminum trichloride, but without the addition of nucleophiles, a slower, but practically quantitative intramolecular cyclization reaction (Scholl reaction [1] ) of 1 to phenanthro[9,10-c]-1,2,5-thiadiazole 1,1-dioxide (3), took place. Both reactions occur through the intermediation of a strong electrophile formed by 1 and aluminum trichloride. Spectral data and structure (through single-crystal X-ray diffraction, with the exception of 2c) were measured for all new compounds.

Key words

Lewis acids - heterocycles - sulfoxides - Scholl reaction - electrophilic aromatic substitutions

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