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Volumn 12, Issue 4, 2010, Pages 668-671

A novel approach to 3-methylindoles by a heck/cyclization/isomerization process

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINATED HYDROCARBON; DRUG DERIVATIVE; MESYLIC ACID DERIVATIVE; SKATOLE;

EID: 76849094529     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol902636v     Document Type: Article
Times cited : (35)

References (32)
  • 4
    • 0003660996 scopus 로고    scopus 로고
    • Li, J. J.; Gribble, G. W., Eds. Pergamon: Oxford, UK
    • (d) Li, J. J.; Gribble, G. W., Eds. Palladium in Heterocyclic Chemistry; Pergamon: Oxford, UK, 2000.
    • (2000) Palladium in Heterocyclic Chemistry
  • 16
    • 0038584673 scopus 로고
    • (b) For a discussion of mechanism and regioselectivity in the Heck reaction, see: Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 2-7
    • Cabri, W.1    Candiani, I.2
  • 18
    • 76849085473 scopus 로고    scopus 로고
    • See the Supporting Information for the synthesis of the chlorotriflates from the corresponding chlorophenols
    • See the Supporting Information for the synthesis of the chlorotriflates from the corresponding chlorophenols.
  • 19
    • 76849097279 scopus 로고    scopus 로고
    • o-Bromo triflates were found to not be as efficient in the Heck reaction
    • o-Bromo triflates were found to not be as efficient in the Heck reaction.
  • 20
    • 76849102605 scopus 로고    scopus 로고
    • For the full table from the base screen, please see the Supporting Information
    • For the full table from the base screen, please see the Supporting Information.
  • 21
    • 76849087677 scopus 로고    scopus 로고
    • CuI (10 mol %) with L-proline (20 mol %) also gave a small amount of the desired methylene-substituted indoline (11%). Attempts to optimize this proved fruitless with messy reaction profiles, forming multiple products
    • CuI (10 mol %) with L-proline (20 mol %) also gave a small amount of the desired methylene-substituted indoline (11%). Attempts to optimize this proved fruitless with messy reaction profiles, forming multiple products.
  • 22
    • 76849102969 scopus 로고    scopus 로고
    • Investigations into a single catalyst system for the Heck reaction and cyclization have so far proved elusive
    • Investigations into a single catalyst system for the Heck reaction and cyclization have so far proved elusive.
  • 24
    • 76849114180 scopus 로고    scopus 로고
    • While it was possible to directly charge CSA at the end of the cyclization reaction, the process benefitted from a quick aqueous workup prior to addition of CSA
    • While it was possible to directly charge CSA at the end of the cyclization reaction, the process benefitted from a quick aqueous workup prior to addition of CSA.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.