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Traceless synthesis of diketopiperazine fused tetrahydro-β-carbolines on soluble polymer support
The Pictet–Spengler reaction, using polyethylene glycol immobilized tryptophan ester with a variety of ketones, was achieved by refluxing condition in acidic chloroform. The linear as well as cyclic ketones were employed. All the ketones were reacted within 6–8 h to furnish soluble polymer-supported...
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| Published in: | Molecular diversity 2011-05, Vol.15 (2), p.569-581 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c343t-978667a8103571dec419d7afd0b8ea242a033c426141f3761738662a61a1ec643 |
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| cites | cdi_FETCH-LOGICAL-c343t-978667a8103571dec419d7afd0b8ea242a033c426141f3761738662a61a1ec643 |
| container_end_page | 581 |
| container_issue | 2 |
| container_start_page | 569 |
| container_title | Molecular diversity |
| container_volume | 15 |
| creator | Chanda, Kaushik Chou, Cheng-Ting Lai, Jin-Ji Lin, Shu-Fen Yellol, Gorakh S. Sun, Chung-Ming |
| description | The Pictet–Spengler reaction, using polyethylene glycol immobilized tryptophan ester with a variety of ketones, was achieved by refluxing condition in acidic chloroform. The linear as well as cyclic ketones were employed. All the ketones were reacted within 6–8 h to furnish soluble polymer-supported tetrahydro-
β
-carboline in good yields. Further expansion at
N
-terminus of tetrahydro-
β
-carbolines was achieved through a reaction with chloroacetyl chloride. Finally, the 2,5-diketopiperazine skeleton was constructed over a
β
-carboline by amination of the resulting
N
-chloroacetamides and subsequent intramolecular cyclization leading to cleavage of the polymer; constitutes a traceless synthesis of tetracyclic molecular architecture. Significantly, this strategy affords a straightforward and efficient approach for the construction of biological promising molecules with high purity and good yields.
Graphical Abstract |
| doi_str_mv | 10.1007/s11030-010-9284-z |
| format | article |
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β
-carboline in good yields. Further expansion at
N
-terminus of tetrahydro-
β
-carbolines was achieved through a reaction with chloroacetyl chloride. Finally, the 2,5-diketopiperazine skeleton was constructed over a
β
-carboline by amination of the resulting
N
-chloroacetamides and subsequent intramolecular cyclization leading to cleavage of the polymer; constitutes a traceless synthesis of tetracyclic molecular architecture. Significantly, this strategy affords a straightforward and efficient approach for the construction of biological promising molecules with high purity and good yields.
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β
-carboline in good yields. Further expansion at
N
-terminus of tetrahydro-
β
-carbolines was achieved through a reaction with chloroacetyl chloride. Finally, the 2,5-diketopiperazine skeleton was constructed over a
β
-carboline by amination of the resulting
N
-chloroacetamides and subsequent intramolecular cyclization leading to cleavage of the polymer; constitutes a traceless synthesis of tetracyclic molecular architecture. Significantly, this strategy affords a straightforward and efficient approach for the construction of biological promising molecules with high purity and good yields.
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β
-carboline in good yields. Further expansion at
N
-terminus of tetrahydro-
β
-carbolines was achieved through a reaction with chloroacetyl chloride. Finally, the 2,5-diketopiperazine skeleton was constructed over a
β
-carboline by amination of the resulting
N
-chloroacetamides and subsequent intramolecular cyclization leading to cleavage of the polymer; constitutes a traceless synthesis of tetracyclic molecular architecture. Significantly, this strategy affords a straightforward and efficient approach for the construction of biological promising molecules with high purity and good yields.
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| identifier | ISSN: 1381-1991 |
| ispartof | Molecular diversity, 2011-05, Vol.15 (2), p.569-581 |
| issn | 1381-1991 1573-501X |
| language | eng |
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| source | Springer Nature |
| subjects | Amines - chemistry Biochemistry Biomedical and Life Sciences Carbolines - chemical synthesis Carbolines - chemistry Combinatorial Chemistry Techniques Diketopiperazines - chemistry Full-Length Paper Ketones - chemistry Life Sciences Models, Chemical Organic Chemistry Pharmacy Polymer Sciences Polymers - chemistry Solubility |
| title | Traceless synthesis of diketopiperazine fused tetrahydro-β-carbolines on soluble polymer support |
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