Ring transformations of β-lactam-condensed 1,3-benzothiazines to isoquinoline and thiazole derivatives by sulfur extrusion and addition sequences

Research output: Article

3 Citations (Scopus)

Abstract

The ring transformations of dichloro-β-lactam-fused 2-aryl-1,3-benzothiazines with sodium methoxide were investigated. With 2 equiv of base, the dichloro-β-lactam derivatives underwent rearrangement and dihydro-1,4-benzothiazepines, 3,4-substituted isoquinolines and substituted thiazole disulfides were isolated. A possible reaction mechanism is proposed for the simultaneous formation of the novel products. The formation of isoquinoline and thiazole derivatives can be explained by sulfur extrusion and addition sequences.

Original languageEnglish
Pages (from-to)6581-6586
Number of pages6
JournalTetrahedron
Volume68
Issue number32
DOIs
Publication statusPublished - aug. 12 2012

Fingerprint

Thiazoles
Lactams
Sulfur
Extrusion
Isoquinolines
Derivatives
Disulfides
Methanol
isoquinoline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Ring transformations of β-lactam-condensed 1,3-benzothiazines to isoquinoline and thiazole derivatives by sulfur extrusion and addition sequences",
abstract = "The ring transformations of dichloro-β-lactam-fused 2-aryl-1,3-benzothiazines with sodium methoxide were investigated. With 2 equiv of base, the dichloro-β-lactam derivatives underwent rearrangement and dihydro-1,4-benzothiazepines, 3,4-substituted isoquinolines and substituted thiazole disulfides were isolated. A possible reaction mechanism is proposed for the simultaneous formation of the novel products. The formation of isoquinoline and thiazole derivatives can be explained by sulfur extrusion and addition sequences.",
keywords = "1,3-Benzothiazine, Benzothiazepine, Dichloro-β-lactam, Isoquinoline, Ring transformation, Thiazole",
author = "L. Fodor and P. Csom{\'o}s and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2012",
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language = "English",
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T1 - Ring transformations of β-lactam-condensed 1,3-benzothiazines to isoquinoline and thiazole derivatives by sulfur extrusion and addition sequences

AU - Fodor, L.

AU - Csomós, P.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2012/8/12

Y1 - 2012/8/12

N2 - The ring transformations of dichloro-β-lactam-fused 2-aryl-1,3-benzothiazines with sodium methoxide were investigated. With 2 equiv of base, the dichloro-β-lactam derivatives underwent rearrangement and dihydro-1,4-benzothiazepines, 3,4-substituted isoquinolines and substituted thiazole disulfides were isolated. A possible reaction mechanism is proposed for the simultaneous formation of the novel products. The formation of isoquinoline and thiazole derivatives can be explained by sulfur extrusion and addition sequences.

AB - The ring transformations of dichloro-β-lactam-fused 2-aryl-1,3-benzothiazines with sodium methoxide were investigated. With 2 equiv of base, the dichloro-β-lactam derivatives underwent rearrangement and dihydro-1,4-benzothiazepines, 3,4-substituted isoquinolines and substituted thiazole disulfides were isolated. A possible reaction mechanism is proposed for the simultaneous formation of the novel products. The formation of isoquinoline and thiazole derivatives can be explained by sulfur extrusion and addition sequences.

KW - 1,3-Benzothiazine

KW - Benzothiazepine

KW - Dichloro-β-lactam

KW - Isoquinoline

KW - Ring transformation

KW - Thiazole

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DO - 10.1016/j.tet.2012.05.033

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JO - Tetrahedron

JF - Tetrahedron

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