Synthesis of helical [2.2]paracyclophanes containing carbocyclic and heterocyclic five-membered rings

Aldo Taticchi, Lucio Minuti, Daniela Lanari, Assunta Marrocchi, Ilaria Tesei, E. Gács-Baitz

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The preparation of a [2.2]indenoparacyclophane-based diene is described. Diels-Alder cycloadditions of this diene with N-methylmaleimide, N-phenylmaleimide and maleic anhydride occurred in good yields and anti-diastereoselectively only under high pressure conditions. Heterohelicenophanes were prepared by dehydrogenation of the Diels-Alder products with 10% Pd/C catalyst. A new helicenophanequinone was obtained by the reaction between the diene and 1,4-naphthoquinone. Graphical Abstract

Original languageEnglish
Pages (from-to)11759-11764
Number of pages6
JournalTetrahedron
Volume60
Issue number51
DOIs
Publication statusPublished - Dec 13 2004

Fingerprint

Maleic Anhydrides
Cycloaddition
Cycloaddition Reaction
Dehydrogenation
Pressure
Catalysts
(2.2)paracyclophane
1,4-naphthoquinone
N-phenylmaleimide
N-methylmaleimide

Keywords

  • Diels-Alder
  • Helical cyclophanes
  • High pressure

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of helical [2.2]paracyclophanes containing carbocyclic and heterocyclic five-membered rings. / Taticchi, Aldo; Minuti, Lucio; Lanari, Daniela; Marrocchi, Assunta; Tesei, Ilaria; Gács-Baitz, E.

In: Tetrahedron, Vol. 60, No. 51, 13.12.2004, p. 11759-11764.

Research output: Contribution to journalArticle

Taticchi, Aldo ; Minuti, Lucio ; Lanari, Daniela ; Marrocchi, Assunta ; Tesei, Ilaria ; Gács-Baitz, E. / Synthesis of helical [2.2]paracyclophanes containing carbocyclic and heterocyclic five-membered rings. In: Tetrahedron. 2004 ; Vol. 60, No. 51. pp. 11759-11764.
@article{a5ef794194484164a1ae231a12f42837,
title = "Synthesis of helical [2.2]paracyclophanes containing carbocyclic and heterocyclic five-membered rings",
abstract = "The preparation of a [2.2]indenoparacyclophane-based diene is described. Diels-Alder cycloadditions of this diene with N-methylmaleimide, N-phenylmaleimide and maleic anhydride occurred in good yields and anti-diastereoselectively only under high pressure conditions. Heterohelicenophanes were prepared by dehydrogenation of the Diels-Alder products with 10{\%} Pd/C catalyst. A new helicenophanequinone was obtained by the reaction between the diene and 1,4-naphthoquinone. Graphical Abstract",
keywords = "Diels-Alder, Helical cyclophanes, High pressure",
author = "Aldo Taticchi and Lucio Minuti and Daniela Lanari and Assunta Marrocchi and Ilaria Tesei and E. G{\'a}cs-Baitz",
year = "2004",
month = "12",
day = "13",
doi = "10.1016/j.tet.2004.09.114",
language = "English",
volume = "60",
pages = "11759--11764",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "51",

}

TY - JOUR

T1 - Synthesis of helical [2.2]paracyclophanes containing carbocyclic and heterocyclic five-membered rings

AU - Taticchi, Aldo

AU - Minuti, Lucio

AU - Lanari, Daniela

AU - Marrocchi, Assunta

AU - Tesei, Ilaria

AU - Gács-Baitz, E.

PY - 2004/12/13

Y1 - 2004/12/13

N2 - The preparation of a [2.2]indenoparacyclophane-based diene is described. Diels-Alder cycloadditions of this diene with N-methylmaleimide, N-phenylmaleimide and maleic anhydride occurred in good yields and anti-diastereoselectively only under high pressure conditions. Heterohelicenophanes were prepared by dehydrogenation of the Diels-Alder products with 10% Pd/C catalyst. A new helicenophanequinone was obtained by the reaction between the diene and 1,4-naphthoquinone. Graphical Abstract

AB - The preparation of a [2.2]indenoparacyclophane-based diene is described. Diels-Alder cycloadditions of this diene with N-methylmaleimide, N-phenylmaleimide and maleic anhydride occurred in good yields and anti-diastereoselectively only under high pressure conditions. Heterohelicenophanes were prepared by dehydrogenation of the Diels-Alder products with 10% Pd/C catalyst. A new helicenophanequinone was obtained by the reaction between the diene and 1,4-naphthoquinone. Graphical Abstract

KW - Diels-Alder

KW - Helical cyclophanes

KW - High pressure

UR - http://www.scopus.com/inward/record.url?scp=8444238902&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=8444238902&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.09.114

DO - 10.1016/j.tet.2004.09.114

M3 - Article

AN - SCOPUS:8444238902

VL - 60

SP - 11759

EP - 11764

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 51

ER -