Reductive smiles rearrangement of 1-[(5-chloro-2-nitrophenyl)sulfonyl]-1H-pyrrole-2-carbohydrazide to 1-amino-6-chloro-2-(1H-pyrrol-2-yl)benzimidazole (Articolo in rivista)

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  • Reductive smiles rearrangement of 1-[(5-chloro-2-nitrophenyl)sulfonyl]-1H-pyrrole-2-carbohydrazide to 1-amino-6-chloro-2-(1H-pyrrol-2-yl)benzimidazole (Articolo in rivista) (literal)
Anno
  • 2000-01-01T00:00:00+01:00 (literal)
Alternative label
  • Silvestri, R; Pifferi, A; De Martino, G; Massa, S; Saturnino, C; Artico, M (2000)
    Reductive smiles rearrangement of 1-[(5-chloro-2-nitrophenyl)sulfonyl]-1H-pyrrole-2-carbohydrazide to 1-amino-6-chloro-2-(1H-pyrrol-2-yl)benzimidazole
    in Heterocycles (Print); Pergamon-Elsevier Science Ltd., Oxford (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Silvestri, R; Pifferi, A; De Martino, G; Massa, S; Saturnino, C; Artico, M (literal)
Pagina inizio
  • 2163 (literal)
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  • 53 (literal)
Rivista
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  • 10 (literal)
Note
  • ISI Web of Science (WOS) (literal)
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  • [ 1 ] Univ Rome La Sapienza, Dipartimento Studi Farmaceut, Inst Pasteur, Fdn Cenci Bolognetti, I-00185 Rome, Italy [ 2 ] CNR, Ist Strutturist Chim, I-00016 Monterotondo, Roma, Italy [ 3 ] Univ Salerno, Dipartimento Sci Farmaceut, I-84084 Penta, Salerno, Italy (literal)
Titolo
  • Reductive smiles rearrangement of 1-[(5-chloro-2-nitrophenyl)sulfonyl]-1H-pyrrole-2-carbohydrazide to 1-amino-6-chloro-2-(1H-pyrrol-2-yl)benzimidazole (literal)
Abstract
  • Treatment of 1-[(5-chloro-2-nitrophenyl)sulfonyl]-1H-pyrrole-2-carbohydrazide with powdered iron in glacial acetic acid afforded 1-amino-6-chloro-2-(1H-pyrrol-2-yl)benzimidazole as the sole product. This compound was also obtained by iron-acetic acid reduction of 1-(5-chloro-2-nitrophenyl)-1H-pyrrole-2-carbohydrazide. Splitting of the sulfone group occurred only in the presence of the carbohydrazide group. In fact, iron-acetic acid reduction of 5-chloro-2-nitrophenyl 2-ethoxycarbonyl-1H-pyrrol-1-yl sulfone gave the expected 2-amino-5-chlorophenyl 2-ethoxycarbonyl-1H-pyrrol-1-yl sulfone. Treatment of this compound with hydrazine yielded the corresponding carbohydrazide, which failed cyclization when reacted with phosphorus pentoxide. Formation of 7-chloropyrrolo[1,2-b] [1,2,5]benzothiadiazepin-11(10H)-one 5,5-dioxide with loss of hydrazine was observed when the above amino hydrazide was reacted with 2-hydroxypyridine or with glacial acetic acid. (literal)
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