A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction
Structurally diverse fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrids were synthesized to get excellent yields via a tandem multi-component reaction sequence employing an environmentally benign solid state melt reaction involving [3+2]-cycloaddition process followed b...
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| Format: | Article |
| Language: | English |
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De Gruyter
2023-07-01
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| Series: | Green Processing and Synthesis |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/gps-2023-0043 |
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| author | Mani Suresh Raju Rajesh Arumugam Natarajan Almansour Abdulrahman I. Suresh Kumar Raju Perumal Karthikeyan |
| author_facet | Mani Suresh Raju Rajesh Arumugam Natarajan Almansour Abdulrahman I. Suresh Kumar Raju Perumal Karthikeyan |
| author_sort | Mani Suresh |
| collection | DOAJ |
| description | Structurally diverse fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrids were synthesized to get excellent yields via a tandem multi-component reaction sequence employing an environmentally benign solid state melt reaction involving [3+2]-cycloaddition process followed by two consecutive annulation steps. Baylis–Hillman products, used as dipolarophiles, were synthesized from various substituted aryl/heteroaryl aldehydes in the presence of DABCO and methyl acrylate, while the 1,3-dipole component was derived in situ from indoline-2,3-dione and acyclic/cyclic amino acid viz N-methylgylcine/l-proline. The structure of the unusual tandem products was unambiguously assigned by spectroscopic and XRD analysis. The products arose through the formation of three new rings, five new bonds, and three adjoining stereocenters with complete diastereomeric control. |
| first_indexed | 2024-03-12T23:16:41Z |
| format | Article |
| id | doaj.art-ae3773aaced949618108185191b22a92 |
| institution | Directory Open Access Journal |
| issn | 2191-9550 |
| language | English |
| last_indexed | 2024-03-12T23:16:41Z |
| publishDate | 2023-07-01 |
| publisher | De Gruyter |
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| series | Green Processing and Synthesis |
| spelling | doaj.art-ae3773aaced949618108185191b22a922023-07-17T05:25:02ZengDe GruyterGreen Processing and Synthesis2191-95502023-07-011215279210.1515/gps-2023-0043A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reactionMani Suresh0Raju Rajesh1Arumugam Natarajan2Almansour Abdulrahman I.3Suresh Kumar Raju4Perumal Karthikeyan5Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai, 600 025, IndiaDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai, 600 025, IndiaDepartment of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, Saudi ArabiaDepartment of Chemistry and Biochemistry, The Ohio State University, 151 W. Woodruff Ave, Columbus, OH 43210, USAStructurally diverse fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrids were synthesized to get excellent yields via a tandem multi-component reaction sequence employing an environmentally benign solid state melt reaction involving [3+2]-cycloaddition process followed by two consecutive annulation steps. Baylis–Hillman products, used as dipolarophiles, were synthesized from various substituted aryl/heteroaryl aldehydes in the presence of DABCO and methyl acrylate, while the 1,3-dipole component was derived in situ from indoline-2,3-dione and acyclic/cyclic amino acid viz N-methylgylcine/l-proline. The structure of the unusual tandem products was unambiguously assigned by spectroscopic and XRD analysis. The products arose through the formation of three new rings, five new bonds, and three adjoining stereocenters with complete diastereomeric control.https://doi.org/10.1515/gps-2023-0043tandem multicomponent reactioneco-friendly protocolsolid state melt reactionpyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone |
| spellingShingle | Mani Suresh Raju Rajesh Arumugam Natarajan Almansour Abdulrahman I. Suresh Kumar Raju Perumal Karthikeyan A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction Green Processing and Synthesis tandem multicomponent reaction eco-friendly protocol solid state melt reaction pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone |
| title | A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction |
| title_full | A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction |
| title_fullStr | A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction |
| title_full_unstemmed | A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction |
| title_short | A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction |
| title_sort | one pot multicomponent tandem synthesis of fused polycyclic pyrrolo 3 2 c quinolinone pyrrolizino 2 3 c quinolinone hybrid heterocycles via environmentally benign solid state melt reaction |
| topic | tandem multicomponent reaction eco-friendly protocol solid state melt reaction pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone |
| url | https://doi.org/10.1515/gps-2023-0043 |
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