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2000
Volume 29, Issue 15
  • ISSN: 1385-2728
  • E-ISSN: 1875-5348

Abstract

Various phenazine scaffolds are reputed for their significant biological activities. The majority of them can be obtained from natural sources. Other phenazine derivatives, especially benzo[]phenazines, are found to possess immense biological efficacies, including antimicrobial, antifungal, anticancer, antileukemic, antitumor activities, Constant efforts have been made to increase the biological efficacies by using fusing benzo[]phenazine skeleton with the other biologically promising heterocycles. Among many others, benzo[]phenazine annulated with pyran skeleton was found to exhibit a wide range of biological efficacies like antimalarial, anti-plasmodial, anticancer, antiangiogenic, anticancer activities, . These observations motivated us to synthesize some benzo[]pyrano[2,3-]phenazine derivatives under greener conditions by following multicomponent reaction strategies. In this study, we report a facile, straightforward, and environmentally benign high-yielding one-pot four-component reaction protocol for the preparation of a series of 3-amino-2-cyano-1-aryl/alkyl-1-benzo[]pyrano[2,3-c]phenazines from the reactions of 2-hydroxy-1,4-naphthaquinone, -phenylenediamines, malononitrile, and aromatic/aliphatic aldehydes using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as an efficient organocatalyst in aqueous ethanol under refluxed conditions. Moreover, under the same optimized reaction conditions, a number of spiro[benzo[]pyrano[2,3-c]phenazine-1,3'-indoline] derivatives were also synthesized in good yields from one-pot four-component reactions of 2-hydroxy-1,4-naphthaquinone, -phenylenediamines, malononitrile, and isatin or substituted isatins.

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2025-09-26

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DBU Catalyzed One-pot Four-component Synthesis of Benzo[a]pyrano[2,3-c]- phenazines and Spiro[benzo[a]pyrano[2,3-c]phenazine-1,3'-indoline] Derivatives
Current Organic Chemistry 29, 1170 (2025); https://doi.org/10.2174/0113852728334531241014075751
/content/journals/coc/10.2174/0113852728334531241014075751
/content/journals/coc/10.2174/0113852728334531241014075751
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Supplements

Scanned spectra, including FTIR, 1H-NMR, 13C-NMR, and HRMS of all the synthesized scaffolds, are supplemented with supporting information. Supplementary material is available on the publisher’s web site along with the published article.

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  • Article Type:     Research Article
Keyword(s): DBU; four-component reactions; green synthesis; organocatalysis; pyran fused benzo[a]phenazines; spiroheterocycles

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