Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes
Abstract Novel tetrahydroisoquinoline and piperidine derivatives were selectively synthesized from substituted indenes or cyclopentenes. The process starts with an oxidative cleavage of the ring olefin bond, which gives reactive diformyl intermediates. By a ring‐closing step using chiral (R) or (S)...
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley-VCH
2025-05-01
|
| Series: | ChemistryOpen |
| Subjects: | |
| Online Access: | https://doi.org/10.1002/open.202400475 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849322488066998272 |
|---|---|
| author | Anas Semghouli László Drahos Jianlin Han Loránd Kiss Melinda Nonn |
| author_facet | Anas Semghouli László Drahos Jianlin Han Loránd Kiss Melinda Nonn |
| author_sort | Anas Semghouli |
| collection | DOAJ |
| description | Abstract Novel tetrahydroisoquinoline and piperidine derivatives were selectively synthesized from substituted indenes or cyclopentenes. The process starts with an oxidative cleavage of the ring olefin bond, which gives reactive diformyl intermediates. By a ring‐closing step using chiral (R) or (S) α‐methylbenzylamine under a reductive amination protocol facilitated ring formation with ring expansion of the corresponding nitrogen‐containing heterocycles. The stereocontrolled methodology enabled accurate control of the stereochemistry of the final products. Additionally, the synthesized amino acid derivatives possessing an aryl moiety in their structure may be relevant building blocks for foldamer chemistry. |
| format | Article |
| id | doaj-art-a529529fea4f40aab3e08edbfed66c23 |
| institution | Kabale University |
| issn | 2191-1363 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj-art-a529529fea4f40aab3e08edbfed66c232025-08-20T03:49:22ZengWiley-VCHChemistryOpen2191-13632025-05-01145n/an/a10.1002/open.202400475Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and CyclopentenesAnas Semghouli0László Drahos1Jianlin Han2Loránd Kiss3Melinda Nonn4Institute of Organic Chemistry Stereochemistry Research Group HUN-REN Research Center for Natural Sciences H-1117 Budapest Magyar tudósok krt. 2 HungaryInstitute of Organic Chemistry MS Proteomics Research Group HUN-REN Research Centre for Natural Sciences H-1117 Budapest Magyar tudósok krt. 2 HungaryJiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources College of Chemical Engineering Nanjing Forestry University Nanjing 210037 ChinaInstitute of Organic Chemistry Stereochemistry Research Group HUN-REN Research Center for Natural Sciences H-1117 Budapest Magyar tudósok krt. 2 HungaryMTA TTK Lendület Artificial Transporter Research Group Institute of Materials and Environmental Chemistry HUN-REN Research Center for Natural Sciences H-1117 Budapest Magyar tudósok krt. 2 HungaryAbstract Novel tetrahydroisoquinoline and piperidine derivatives were selectively synthesized from substituted indenes or cyclopentenes. The process starts with an oxidative cleavage of the ring olefin bond, which gives reactive diformyl intermediates. By a ring‐closing step using chiral (R) or (S) α‐methylbenzylamine under a reductive amination protocol facilitated ring formation with ring expansion of the corresponding nitrogen‐containing heterocycles. The stereocontrolled methodology enabled accurate control of the stereochemistry of the final products. Additionally, the synthesized amino acid derivatives possessing an aryl moiety in their structure may be relevant building blocks for foldamer chemistry.https://doi.org/10.1002/open.202400475CyclizationRing expansionRing openingRing closingPiperidineTetrahydroisoquinoline |
| spellingShingle | Anas Semghouli László Drahos Jianlin Han Loránd Kiss Melinda Nonn Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes ChemistryOpen Cyclization Ring expansion Ring opening Ring closing Piperidine Tetrahydroisoquinoline |
| title | Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes |
| title_full | Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes |
| title_fullStr | Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes |
| title_full_unstemmed | Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes |
| title_short | Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes |
| title_sort | selective synthesis of tetrahydroisoquinoline and piperidine scaffolds by oxidative ring opening ring closing protocols of substituted indenes and cyclopentenes |
| topic | Cyclization Ring expansion Ring opening Ring closing Piperidine Tetrahydroisoquinoline |
| url | https://doi.org/10.1002/open.202400475 |
| work_keys_str_mv | AT anassemghouli selectivesynthesisoftetrahydroisoquinolineandpiperidinescaffoldsbyoxidativeringopeningringclosingprotocolsofsubstitutedindenesandcyclopentenes AT laszlodrahos selectivesynthesisoftetrahydroisoquinolineandpiperidinescaffoldsbyoxidativeringopeningringclosingprotocolsofsubstitutedindenesandcyclopentenes AT jianlinhan selectivesynthesisoftetrahydroisoquinolineandpiperidinescaffoldsbyoxidativeringopeningringclosingprotocolsofsubstitutedindenesandcyclopentenes AT lorandkiss selectivesynthesisoftetrahydroisoquinolineandpiperidinescaffoldsbyoxidativeringopeningringclosingprotocolsofsubstitutedindenesandcyclopentenes AT melindanonn selectivesynthesisoftetrahydroisoquinolineandpiperidinescaffoldsbyoxidativeringopeningringclosingprotocolsofsubstitutedindenesandcyclopentenes |