An efficient method for the traceless solid phase synthesis of 2,3-disubstituted indoles using a THP linker and a Pd(0)-mediated annulation of 2-iodoaniline and acetylenes is reported.
Efficient solid-phase synthesis of 2,3-substituted indoles
โ Scribed by Dean A Wacker; Padmaja Kasireddy
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 65 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The development of the solid-phase version of the modified Madelung indole synthesis is reported. The chemistry was initiated with the reductive amination of Bal resin using an ortho substituted aniline. The resin bound aniline was acylated with a variety of acid chlorides followed by cyclization with base to provide the desired indole after TFA-promoted cleavage from the resin.
๐ SIMILAR VOLUMES
Thepslladitmwatafyzed sriidphase synthesis of hi-substituted Moles is deserikd. The synthesis incorporates threeintfepemlemly variable groups andis ideallysuitedfor the preparation of combinatorial libmries.@ 1997Elsevier Science Ltd.
## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a โFull Textโ option. The original article is trackable v
2-Aryl-3-alkylindoles were prepared on solid phase via palladium-mediated heteroannulation of 1-alkyl-2-(trimethylsilyl)acetylene with amide resin-bound o-iodoaniline 1, followed by transformation of trimethylsilyl to iodide and then Suzuki coupling reactions. Traceless synthesis of symmetrical and
AbstractรAn efยฎcient method for the solid phase synthesis of 1,6-disubstituted 2,3-diketopiperazine and 1,4,5-trisubstituted 2,3-diketopiperazine derivatives is described. The reduction of resin-bound acylated amino acids or resin-bound acylated dipeptides, followed by treatment with oxalyldiimidazo