A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-<i>c</i>]quinolinone/pyrrolizino[2,3-<i>c</i>]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction-Reference-Cited by-同舟云学术

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

Published:2023-01-01 Issue:1 Volume:12 Page:
ISSN:2191-9550
Container-title:Green Processing and Synthesis
language:en
Short-container-title:

Author:

Mani Suresh¹,Raju Rajesh¹,Arumugam Natarajan²,Almansour Abdulrahman I.²,Suresh Kumar Raju²,Perumal Karthikeyan³

Affiliation:

1. Department of Organic Chemistry, University of Madras, Guindy Campus , Chennai , 600 025 , India

2. Department of Chemistry, College of Science, King Saud University , P. O. Box 2455 , Riyadh , Saudi Arabia

3. Department of Chemistry and Biochemistry, The Ohio State University , 151 W. Woodruff Ave , Columbus , OH 43210 , USA

Abstract

Abstract 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.

Publisher

Walter de Gruyter GmbH

Subject

Health, Toxicology and Mutagenesis,Industrial and Manufacturing Engineering,Fuel Technology,Renewable Energy, Sustainability and the Environment,General Chemical Engineering,Environmental Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/gps-2023-0043/pdf

Reference30 articles.

1. Murlykina MV, Morozova AD, Zviagin IM, Sakhno YI, Desenko SM, Chebanov1 VA. Aminoazole-based diversity-oriented synthesis of heterocycles. Front Chem. 2018;6:527.

2. Moroz AA, Zhulanov VE, Dmitriev MV, Maslivets AN. Diversity-oriented synthesis of three skeletally diverse iminolactones from isocyanides, activated acetylenes and 1H-pyrrole-2,3-diones via [3+2] and [4+1] cycloaddition reactions. Tetrahedron. 2020;76:130880.

3. Das S. Recent applications of 1,3-indanedione in organic transformations for the construction of fused- and spiro scaffolds. Tetrahedron. 2022;122:132954.

4. Maharani S, Almansour AI, Suresh Kumar R, Arumugam N, Ranjith Kumar R. Synthesis of cycloalkano[b]pyridines by multicomponent strategy: ring-size mediated product selectivity, substitution-induced axial chirality and influence of the 14N quadrupole-relaxation. Tetrahedron. 2016;72:4582–92.

5. Mani S, Raju R, Raghunathan R, Arumugam N, Almansour AI, Suresh Kumar R, et al. Environmentally friendly domino multicomponent strategy for the synthesis of pyrroloquinolinone hybrid heterocycles. RSC Adv. 2022;12:15440–6.