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Volumn 13, Issue 2, 2011, Pages 320-323

Safe and reliable synthesis of diazoketones and quinoxalines in a continuous flow reactor

Author keywords

[No Author keywords available]

Indexed keywords

DIAZONIUM COMPOUND; KETONE; PHENYLENEDIAMINE DERIVATIVE; QUINOXALINE DERIVATIVE;

EID: 78651474657     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1027927     Document Type: Article
Times cited : (138)

References (40)
  • 5
    • 78651507839 scopus 로고    scopus 로고
    • e-EROS Encyclopedia of Reagents for Organic Synthesis
    • Shiori, T.; Aoyama, T.; Snowden, T. e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001.
    • (2001)
    • Shiori, T.1    Aoyama, T.2    Snowden, T.3
  • 6
    • 78651501136 scopus 로고    scopus 로고
    • http://www.canadaeast.com/front/article/666039.
  • 16
    • 78651518595 scopus 로고    scopus 로고
    • Industrial scale continuous diazomethane production is carried out by Phoenix Chemicals: US6962983. This is achieved by feeding a base and diazomethane precursor into a reactor vessel that generates diazomethane which can be removed using a diluent gas
    • Industrial scale continuous diazomethane production is carried out by Phoenix Chemicals: US6962983. This is achieved by feeding a base and diazomethane precursor into a reactor vessel that generates diazomethane which can be removed using a diluent gas.
  • 19
    • 78651486257 scopus 로고    scopus 로고
    • PS-Diazald was prepared from a commercially available polymer-supported tosyl chloride in two steps: see Supporting Information
    • PS-Diazald was prepared from a commercially available polymer-supported tosyl chloride in two steps: see Supporting Information.
  • 20
    • 78651469217 scopus 로고    scopus 로고
    • Flow Liquid Liquid Extraction machine, available from Syrris
    • Flow Liquid Liquid Extraction machine, available from Syrris, http://www.syrris.com.
  • 21
    • 78651496926 scopus 로고    scopus 로고
    • http://www.vapourtec.co.uk.
  • 23
    • 78651470037 scopus 로고    scopus 로고
    • Similar results were obtained starting from 3-phenyl propionyl chloride 1a; we observed formation of the expected diazoketone 2a (62%) and the TMS-protected diazoketone (31%)
    • Similar results were obtained starting from 3-phenyl propionyl chloride 1a; we observed formation of the expected diazoketone 2a (62%) and the TMS-protected diazoketone (31%).
  • 24
    • 78651510350 scopus 로고    scopus 로고
    • A23: 2-3 mmol, commercially available from Sigma-Aldrich
    • A23: 2-3 mmol, commercially available from Sigma-Aldrich.
  • 25
    • 78651510048 scopus 로고    scopus 로고
    • Except for 2e, 2g, 2h, and 2i: crude reaction mixtures gave purities >85%; a batch purification was carried out for these compounds (see footnote Scheme 2)
    • Except for 2e, 2g, 2h, and 2i: crude reaction mixtures gave purities >85%; a batch purification was carried out for these compounds (see footnote Scheme 2).
  • 38
    • 78651502781 scopus 로고    scopus 로고
    • With cupric acetylacetonate or rhodium octanoate dimer: only recovered diazoketone was obsereved. With rhodium acetate dimer, numerous side products were identified starting from 2a
    • With cupric acetylacetonate or rhodium octanoate dimer: only recovered diazoketone was obsereved. With rhodium acetate dimer, numerous side products were identified starting from 2a.
  • 39
    • 78651508699 scopus 로고    scopus 로고
    • Crude mixture 4a -4d presented an unidentified impurity which could not be removed using scavengers. Purification was carried out by a catch and release technique: see Supporting Information
    • Crude mixture 4a -4d presented an unidentified impurity which could not be removed using scavengers. Purification was carried out by a catch and release technique: see Supporting Information.
  • 40
    • 78651488596 scopus 로고    scopus 로고
    • Attempts to preferentially form one of the regioisomers by forming one imine as a first step by dehydration of the flow stream failed
    • Attempts to preferentially form one of the regioisomers by forming one imine as a first step by dehydration of the flow stream failed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.