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| Title: | Organocatalysed Michael addition on arylmethylidenemalonates involving 4-(2-nitrophenyl)acetoacetate: Diversity-oriented access to 8,9-dihydropyrido[1,2-a]indol-6(7H)-one and salicylate scaffolds |
| Authors: | Biswas, Soumen Mobin, Shaikh M. Samanta, Sampak |
| Keywords: | Addition reactions;Scaffolds;Aerobic condition;Cycloaromatization;Diastereoselective;Michael additions;Michael adducts;One-pot synthesis;Sterically demanding;Tandem reaction;Synthesis (chemical) |
| Issue Date: | 2015 |
| Publisher: | Royal Society of Chemistry |
| Citation: | Srivastava, A., Biswas, S., Singh, S., Mobin, S. M., & Samanta, S. (2015). Organocatalysed michael addition on arylmethylidenemalonates involving 4-(2-nitrophenyl)acetoacetate: Diversity-oriented access to 8,9-dihydropyrido[1,2-a]indol-6(7H)-one and salicylate scaffolds. RSC Advances, 5(34), 26891-26896. doi:10.1039/c5ra01430a |
| Abstract: | Excellent diastereoselective (≤96:4) preparation of new functionalized 7,8,9-trisubstituted-8,9-dihydropyrido[1,2-a]indol-6(7H)-ones has been achieved in 61-81% yields through a one-pot reductive cycloaromatization-lactamization sequence reaction of Michael adducts using Zn/NH4Cl as a reducing agent. In addition, one-pot synthesis of sterically demanding hexa-substituted salicylate derivatives has been successfully realized via a tandem reaction of alkylidene malonates or aldehydes with 2-nitrophenyl-β-keto ester under aerobic conditions using DBU as an organocatalyst. © The Royal Society of Chemistry 2015. |
| URI: | https://doi.org/10.1039/c5ra01430a https://dspace.iiti.ac.in/handle/123456789/9320 |
| ISSN: | 2046-2069 |
| Type of Material: | Journal Article |
| Appears in Collections: | Department of Chemistry |
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