Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones
The synthesis of multifunctionalized dihydropyridinones from aldehydes and ketones involves at least a three-step process, making route shortening a challenging task, especially in achieving a one-pot four-component synthesis via aldehydes and ketones precondensation. Herein, we discovered a [1 + 2...
Saved in:
| Main Author: | |
|---|---|
| Other Authors: | , , , , , |
| Published: |
2024
|
| Subjects: | |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1852025886962876416 |
|---|---|
| author | Hao Lu (354247) |
| author2 | Xinyu Li (568185) Zhiqing Wang (830081) Peng Du (193248) Shuang-Feng Yin (1478986) Nobuaki Kambe (1621282) Renhua Qiu (1478992) |
| author2_role | author author author author author author |
| author_facet | Hao Lu (354247) Xinyu Li (568185) Zhiqing Wang (830081) Peng Du (193248) Shuang-Feng Yin (1478986) Nobuaki Kambe (1621282) Renhua Qiu (1478992) |
| author_role | author |
| dc.creator.none.fl_str_mv | Hao Lu (354247) Xinyu Li (568185) Zhiqing Wang (830081) Peng Du (193248) Shuang-Feng Yin (1478986) Nobuaki Kambe (1621282) Renhua Qiu (1478992) |
| dc.date.none.fl_str_mv | 2024-10-17T15:36:38Z |
| dc.identifier.none.fl_str_mv | 10.1021/acs.joc.4c01636.s008 |
| dc.relation.none.fl_str_mv | https://figshare.com/articles/dataset/Base-Promoted_One-Pot_Four-Component_Domino_Strategy_Involving_Aldehydes_and_Ketones_to_Access_Multifunctionalized_Dihydropyridinones/27249456 |
| dc.rights.none.fl_str_mv | CC BY-NC 4.0 info:eu-repo/semantics/openAccess |
| dc.subject.none.fl_str_mv | Biochemistry Genetics Physiology Pharmacology Biotechnology Ecology Immunology Infectious Diseases Space Science Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified Information Systems not elsewhere classified oac ), respectively making route shortening initially combining aldehydes commercially available ketones 4 </ sub access multifunctionalized dihydropyridinones multifunctionalized dihydropyridinones rapid access tetrasubstituted pyridines step process novel concept meldrum ’ ketones precondensation ketones involves derived heterocycles conveniently converted challenging task ammonium acetate |
| dc.title.none.fl_str_mv | Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones |
| dc.type.none.fl_str_mv | Dataset info:eu-repo/semantics/publishedVersion dataset |
| description | The synthesis of multifunctionalized dihydropyridinones from aldehydes and ketones involves at least a three-step process, making route shortening a challenging task, especially in achieving a one-pot four-component synthesis via aldehydes and ketones precondensation. Herein, we discovered a [1 + 2 + 1 + 2] four-component domino cyclization reaction, a novel concept in 4CRs with commercially available ketones and aldehydes, which by initially combining aldehydes and ketones with Meldrum’s acid and ammonium acetate (NH<sub>4</sub>OAc), respectively, they give dihydropyridones (>110 examples). This transformation features inexpensive additives and readily available starting materials, making it appropriate for rapid access to relevant pharmaceutical molecules containing dihydropyridinone-derived heterocycles. Also these compounds can be conveniently converted into trisubstituted and tetrasubstituted pyridines. |
| eu_rights_str_mv | openAccess |
| id | Manara_c68898cd5d4fe4f7d5b82346df25df2d |
| identifier_str_mv | 10.1021/acs.joc.4c01636.s008 |
| network_acronym_str | Manara |
| network_name_str | ManaraRepo |
| oai_identifier_str | oai:figshare.com:article/27249456 |
| publishDate | 2024 |
| repository.mail.fl_str_mv | |
| repository.name.fl_str_mv | |
| repository_id_str | |
| rights_invalid_str_mv | CC BY-NC 4.0 |
| spelling | Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized DihydropyridinonesHao Lu (354247)Xinyu Li (568185)Zhiqing Wang (830081)Peng Du (193248)Shuang-Feng Yin (1478986)Nobuaki Kambe (1621282)Renhua Qiu (1478992)BiochemistryGeneticsPhysiologyPharmacologyBiotechnologyEcologyImmunologyInfectious DiseasesSpace ScienceBiological Sciences not elsewhere classifiedChemical Sciences not elsewhere classifiedInformation Systems not elsewhere classifiedoac ), respectivelymaking route shorteninginitially combining aldehydescommercially available ketones4 </ subaccess multifunctionalized dihydropyridinonesmultifunctionalized dihydropyridinonesrapid accesstetrasubstituted pyridinesstep processnovel conceptmeldrum ’ketones precondensationketones involvesderived heterocyclesconveniently convertedchallenging taskammonium acetateThe synthesis of multifunctionalized dihydropyridinones from aldehydes and ketones involves at least a three-step process, making route shortening a challenging task, especially in achieving a one-pot four-component synthesis via aldehydes and ketones precondensation. Herein, we discovered a [1 + 2 + 1 + 2] four-component domino cyclization reaction, a novel concept in 4CRs with commercially available ketones and aldehydes, which by initially combining aldehydes and ketones with Meldrum’s acid and ammonium acetate (NH<sub>4</sub>OAc), respectively, they give dihydropyridones (>110 examples). This transformation features inexpensive additives and readily available starting materials, making it appropriate for rapid access to relevant pharmaceutical molecules containing dihydropyridinone-derived heterocycles. Also these compounds can be conveniently converted into trisubstituted and tetrasubstituted pyridines.2024-10-17T15:36:38ZDatasetinfo:eu-repo/semantics/publishedVersiondataset10.1021/acs.joc.4c01636.s008https://figshare.com/articles/dataset/Base-Promoted_One-Pot_Four-Component_Domino_Strategy_Involving_Aldehydes_and_Ketones_to_Access_Multifunctionalized_Dihydropyridinones/27249456CC BY-NC 4.0info:eu-repo/semantics/openAccessoai:figshare.com:article/272494562024-10-17T15:36:38Z |
| spellingShingle | Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones Hao Lu (354247) Biochemistry Genetics Physiology Pharmacology Biotechnology Ecology Immunology Infectious Diseases Space Science Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified Information Systems not elsewhere classified oac ), respectively making route shortening initially combining aldehydes commercially available ketones 4 </ sub access multifunctionalized dihydropyridinones multifunctionalized dihydropyridinones rapid access tetrasubstituted pyridines step process novel concept meldrum ’ ketones precondensation ketones involves derived heterocycles conveniently converted challenging task ammonium acetate |
| status_str | publishedVersion |
| title | Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones |
| title_full | Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones |
| title_fullStr | Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones |
| title_full_unstemmed | Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones |
| title_short | Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones |
| title_sort | Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones |
| topic | Biochemistry Genetics Physiology Pharmacology Biotechnology Ecology Immunology Infectious Diseases Space Science Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified Information Systems not elsewhere classified oac ), respectively making route shortening initially combining aldehydes commercially available ketones 4 </ sub access multifunctionalized dihydropyridinones multifunctionalized dihydropyridinones rapid access tetrasubstituted pyridines step process novel concept meldrum ’ ketones precondensation ketones involves derived heterocycles conveniently converted challenging task ammonium acetate |