Novel indole syntheses by ring transformation of β-lactam-condensed 1,3-benzothiazines into indolo[2,3-b][1,4]benzothiazepines and indolo[3,2-c]isoquinolines

Research output: Article

7 Citations (Scopus)

Abstract

ortho-Nitrophenyl-substituted condensed 1,3-benzothiazines proved to be a useful core unit in indole syntheses under non-reductive conditions. Thus, the treatment of ortho-nitro-2-aryl-2a-chloro-4H-azeto[2,1-b][1,3]benzothiazin-1- ones with sodium methoxide in methanol provided indolo-1,4-benzothiazepines via a novel rearrangement. Through the sulfur extrusion reaction of indolo[2,3-b][1,4]benzothiazepines, further alkaloid-type indole derivatives, indolo[3,2-c]isoquinolines, were obtained. The structures of the new ring systems were determined by means of NMR spectroscopy.

Original languageEnglish
Pages (from-to)851-856
Number of pages6
JournalTetrahedron
Volume68
Issue number3
DOIs
Publication statusPublished - jan. 21 2012

Fingerprint

Isoquinolines
Lactams
Methanol
Indole Alkaloids
Sulfur
Nuclear magnetic resonance spectroscopy
Extrusion
Magnetic Resonance Spectroscopy
Derivatives
indole

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{e201dea8ad1540ca81a04446c2443098,
title = "Novel indole syntheses by ring transformation of β-lactam-condensed 1,3-benzothiazines into indolo[2,3-b][1,4]benzothiazepines and indolo[3,2-c]isoquinolines",
abstract = "ortho-Nitrophenyl-substituted condensed 1,3-benzothiazines proved to be a useful core unit in indole syntheses under non-reductive conditions. Thus, the treatment of ortho-nitro-2-aryl-2a-chloro-4H-azeto[2,1-b][1,3]benzothiazin-1- ones with sodium methoxide in methanol provided indolo-1,4-benzothiazepines via a novel rearrangement. Through the sulfur extrusion reaction of indolo[2,3-b][1,4]benzothiazepines, further alkaloid-type indole derivatives, indolo[3,2-c]isoquinolines, were obtained. The structures of the new ring systems were determined by means of NMR spectroscopy.",
keywords = "β-Lactam, 1,3-Benzothiazine, Indole synthesis, Indolo-1,4-benzothiazepine, Indolo[3,2-c]isoquinoline, IR, H and C NMR, Ring transformation",
author = "L. Fodor and P. Csom{\'o}s and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2012",
month = "1",
day = "21",
doi = "10.1016/j.tet.2011.11.036",
language = "English",
volume = "68",
pages = "851--856",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "3",

}

TY - JOUR

T1 - Novel indole syntheses by ring transformation of β-lactam-condensed 1,3-benzothiazines into indolo[2,3-b][1,4]benzothiazepines and indolo[3,2-c]isoquinolines

AU - Fodor, L.

AU - Csomós, P.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2012/1/21

Y1 - 2012/1/21

N2 - ortho-Nitrophenyl-substituted condensed 1,3-benzothiazines proved to be a useful core unit in indole syntheses under non-reductive conditions. Thus, the treatment of ortho-nitro-2-aryl-2a-chloro-4H-azeto[2,1-b][1,3]benzothiazin-1- ones with sodium methoxide in methanol provided indolo-1,4-benzothiazepines via a novel rearrangement. Through the sulfur extrusion reaction of indolo[2,3-b][1,4]benzothiazepines, further alkaloid-type indole derivatives, indolo[3,2-c]isoquinolines, were obtained. The structures of the new ring systems were determined by means of NMR spectroscopy.

AB - ortho-Nitrophenyl-substituted condensed 1,3-benzothiazines proved to be a useful core unit in indole syntheses under non-reductive conditions. Thus, the treatment of ortho-nitro-2-aryl-2a-chloro-4H-azeto[2,1-b][1,3]benzothiazin-1- ones with sodium methoxide in methanol provided indolo-1,4-benzothiazepines via a novel rearrangement. Through the sulfur extrusion reaction of indolo[2,3-b][1,4]benzothiazepines, further alkaloid-type indole derivatives, indolo[3,2-c]isoquinolines, were obtained. The structures of the new ring systems were determined by means of NMR spectroscopy.

KW - β-Lactam

KW - 1,3-Benzothiazine

KW - Indole synthesis

KW - Indolo-1,4-benzothiazepine

KW - Indolo[3,2-c]isoquinoline

KW - IR, H and C NMR

KW - Ring transformation

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U2 - 10.1016/j.tet.2011.11.036

DO - 10.1016/j.tet.2011.11.036

M3 - Article

VL - 68

SP - 851

EP - 856

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 3

ER -