• Home
  • Search Results
  • A one-pot synthesis of 7-phenylindolo[3,2-a]carbazoles from indoles and β-nitrostyrenes, via an unprecedented reaction sequence.

A one-pot synthesis of 7-phenylindolo[3,2-a]carbazoles from indoles and β-nitrostyrenes, via an unprecedented reaction sequence.

Organic & biomolecular chemistry (2011-10-07)
Grégory Dupeyre, Pascale Lemoine, Nabila Ainseba, Sylvie Michel, Xavier Cachet
ABSTRACT

A six-step one-pot reaction was designed for synthesizing homodimeric 7-phenylindolo[3,2-a]carbazoles from 1H-indoles and β-nitrostyrenes, in the presence of SnCl(2)·2H(2)O. The reactions proceeded under very mild conditions and the desired heterocycles were obtained in moderate to good yields. An unprecedented mechanism involving sequential indole dimerization, regioselective nucleophilic conjugate addition of the resulting 2,3'-biindole to β-nitrostyrene and formal intramolecular [4 + 2]-cycloaddition is proposed.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tin(II) chloride, reagent grade, 98%
Sigma-Aldrich
Tin(II) chloride dihydrate, ACS reagent, 98%
Sigma-Aldrich
Tin(II) chloride dihydrate, reagent grade, 98%
Sigma-Aldrich
Tin(II) chloride, anhydrous, powder, ≥99.99% trace metals basis
Sigma-Aldrich
Tin(II) chloride dihydrate, ≥99.995% trace metals basis
Sigma-Aldrich
Tin(II) chloride dihydrate, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥98%
Sigma-Aldrich
Tin(II) chloride, ≥99.99% trace metals basis
Supelco
Tin(II) chloride dihydrate, suitable for AAS
Sigma-Aldrich
trans-β-Nitrostyrene, 99%
Sigma-Aldrich
Tin(II) chloride dihydrate, ≥99.99% trace metals basis