Application of the Pictet-Spengler reaction to aryl amine-based substrates having pyrimidine as a pi-nucleophile: Synthesis of pyrimidoquinolines with structural analogy to benzonaphthyridines present in alkaloids
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Agarwal, P K
Sharma, S K Sawant, Devesh Kundu, Bijoy |
|
| Date |
2010-09-20T11:11:18Z
2010-09-20T11:11:18Z 2009 |
|
| Identifier |
Tetrahedron, 65, 6, 2009, 1153-1161
http://hdl.handle.net/123456789/611 |
|
| Description |
Synthesis of pyrimidine annulated quinolines, structurally analogous to biologically active benzonaphthyridines present in alkaloids, has been described. Our synthetic strategy is based on the modified Pictet-Spengler reaction involving substrates comprising deactivated pyrimidine ring as the nucleophilic partner whereas aryl amine originating from the C-4 of the pyrimidine ring served as the source for electrophilic partner. The resulting substrates 5-7 with diversity at 2 and 6-positions after condensation with a variety of aldehydes underwent 6-endo cyclization to furnish pyrimido[5,4-c]quinolines 14 in good yields. However, attempts to further extend this strategy on new structurally analogous substrate, involving the pyridine ring as nucleophilic partner failed; thus limiting the scope of the reaction.
|
|
| Format |
139319 bytes
application/pdf |
|
| Language |
en
|
|
| Subject |
pyrimidine annulated quinolines
Pictet-Spengler reaction tryptamine/tryptophan iminium/electrophilic pi-cyclizations 6-endo cyclization |
|
| Title |
Application of the Pictet-Spengler reaction to aryl amine-based substrates having pyrimidine as a pi-nucleophile: Synthesis of pyrimidoquinolines with structural analogy to benzonaphthyridines present in alkaloids
|
|
| Type |
Article
|
|