Copper-phenanthroline catalysts for regioselective synthesis of pyrrolo[3',4':3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions
A new series of pyrrolo[3',4':3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and pyrrolo[1,2-a]phenanthrolines were efficiently built up from an 8-hydroxyquinoline derivative or phenanthroline via 1,3-dipolar cycloaddition reaction involving non-stabilized azomethine ylides, generated in...
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| Published in | Beilstein journal of organic chemistry Vol. 10; no. 1; pp. 692 - 700 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
Beilstein-Institut
20.03.2014
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| Abstract | A new series of pyrrolo[3',4':3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and pyrrolo[1,2-a]phenanthrolines were efficiently built up from an 8-hydroxyquinoline derivative or phenanthroline via 1,3-dipolar cycloaddition reaction involving non-stabilized azomethine ylides, generated in situ from the parent furo[3,2-h]quinoliniums/phenanthroliums, in presence of a copper(II) chloride-phenanthroline catalytic system. The methodology combines general applicability with high yields. |
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| AbstractList | A new series of pyrrolo[3′,4′:3,4]pyrrolo[1,2-
a
]furoquinolines/phenanthrolines and pyrrolo[1,2-
a
]phenanthrolines were efficiently built up from an 8-hydroxyquinoline derivative or phenanthroline via 1,3-dipolar cycloaddition reaction involving non-stabilized azomethine ylides, generated in situ from the parent furo[3,2-
h
]quinoliniums/phenanthroliums, in presence of a copper(II) chloride–phenanthroline catalytic system. The methodology combines general applicability with high yields. A new series of pyrrolo[3',4':3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and pyrrolo[1,2-a]phenanthrolines were efficiently built up from an 8-hydroxyquinoline derivative or phenanthroline via 1,3-dipolar cycloaddition reaction involving non-stabilized azomethine ylides, generated in situ from the parent furo[3,2-h]quinoliniums/phenanthroliums, in presence of a copper(II) chloride-phenanthroline catalytic system. The methodology combines general applicability with high yields. |
| Author | Anwar, Tarique Kundu, Sandip Hazra, Abhijit Maulik, Prakas R Paira, Rupankar Bharitkar, Yogesh P Mondal, Nirup B Banerjee, Maitreyee Mondal, Shyamal |
| AuthorAffiliation | 1 Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India |
| AuthorAffiliation_xml | – name: 1 Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India |
| Author_xml | – sequence: 1 givenname: Rupankar surname: Paira fullname: Paira, Rupankar organization: Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India – sequence: 2 givenname: Tarique surname: Anwar fullname: Anwar, Tarique organization: Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India – sequence: 3 givenname: Maitreyee surname: Banerjee fullname: Banerjee, Maitreyee organization: Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India – sequence: 4 givenname: Yogesh P surname: Bharitkar fullname: Bharitkar, Yogesh P organization: Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India – sequence: 5 givenname: Shyamal surname: Mondal fullname: Mondal, Shyamal organization: Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India – sequence: 6 givenname: Sandip surname: Kundu fullname: Kundu, Sandip organization: Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India – sequence: 7 givenname: Abhijit surname: Hazra fullname: Hazra, Abhijit organization: Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India – sequence: 8 givenname: Prakas R surname: Maulik fullname: Maulik, Prakas R organization: Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India – sequence: 9 givenname: Nirup B surname: Mondal fullname: Mondal, Nirup B organization: Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India |
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| Keywords | phenanthroliums furo[3,2-h]quinoliniums copper(II) chloride–phenanthroline pyrrolo[1,2-a]phenanthrolines pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines 1,3-dipolar cycloaddition |
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| Snippet | A new series of pyrrolo[3',4':3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and pyrrolo[1,2-a]phenanthrolines were efficiently built up from an... A new series of pyrrolo[3′,4′:3,4]pyrrolo[1,2- a ]furoquinolines/phenanthrolines and pyrrolo[1,2- a ]phenanthrolines were efficiently built up from an... A new series of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and pyrrolo[1,2-a]phenanthrolines were efficiently built up from an... |
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| Title | Copper-phenanthroline catalysts for regioselective synthesis of pyrrolo[3',4':3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions |
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