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Volumn 15, Issue 4, 2011, Pages 918-924

Convenient and practical one-pot synthesis of 4-chloropyrimidines via a novel chloroimidate annulation

Author keywords

[No Author keywords available]

Indexed keywords

DIFFERENT SUBSTRATES; MULTI-STEP; ONE POT; ONE-POT REACTION; ONE-POT SYNTHESIS;

EID: 79960511075     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op1002352     Document Type: Article
Times cited : (16)

References (31)
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    • Microwave-assisted chlorination of hydroxyheteroaromatics using phosphonium salts has also been reported: Tanji, K.-I.; Koshio, J.; Sugimoto, O. Synthesis 2005, 35, 1983
    • (2005) Synthesis , vol.35 , pp. 1983
    • Tanji, K.-I.1    Koshio, J.2    Sugimoto, O.3
  • 16
    • 79960547158 scopus 로고
    • Ger. Pat. Appl. DE 2140986A1
    • Breuer, H.; Schulze, E. Ger. Pat. Appl. DE 2140986A1, 1972.
    • (1972)
    • Breuer, H.1    Schulze, E.2
  • 17
    • 79960506885 scopus 로고
    • Ger. Pat. Appl. DE 2408906A1
    • Breuer, H.; Treuner, U. D. Ger. Pat. Appl. DE 2408906A1, 1974.
    • (1974)
    • Breuer, H.1    Treuner, U.D.2
  • 24
    • 0002886220 scopus 로고
    • Patai, S., Ed.; Interscience Publishers: London, New York
    • To the best of our knowledge, this "inversed reactivity" chloroimidate cyclization reaction has not been reported before (SciFinder, Beilstein Searches, June 2010); all literature references for the overall transformation consist of multistep nitrile hydrolysis/cyclization/chlorination sequences (see refs 6-11]). Chloroimidates are highly reactive C -electrophiles and typically serve as acid chloride surrogates (cf. Vilsmeyer reagents/Vilsmeyer reaction); for reviews, see: Bonnett, R. Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Interscience Publishers: London, New York, 1970; p 597.
    • (1970) Chemistry of the Carbon-Nitrogen Double Bond , pp. 597
    • Bonnett, R.1
  • 26
    • 6444220837 scopus 로고
    • Following an extensive literature search, to our surprise, only a single example of a related ring closure could be found, albeit for a phosphaheteroaromatic Schmidpeter, A.; Schindler, N. Chem. Ber. 1969, 102, 2201
    • (1969) Chem. Ber. , vol.102 , pp. 2201
    • Schmidpeter, A.1    Schindler, N.2
  • 27
    • 79960520178 scopus 로고    scopus 로고
    • Int. Pat. Appl. WO 02076976A2
    • (Cyclization of a p -chloro- N -(2-cyanophenyl)-phosphinimine hydrochloride salt to a 2-phosphaquinazoline system). At this point, we have no evidence to exclude the possibility of a 6π-electrocyclic ring closure. An earlier attempt to achieve this valuable transformation via intramolecular transfer of HCl from an aromatic amidinium hydrochloride salt to a neighboring nitrile group and subsequent cyclization to the 4-chloroquinazoline met with only limited success (25% yield after chromatogr. purification of the product mixture): Nagarathnam, D.; Asgari, D.; Shao, J.; Liu, X.-G.; Khire, U.; Wang, C.; Hart, B.; Boyer, S.; Weber, O.; Lynch, M.; Bankston, D. Int. Pat. Appl. WO 02076976A2, 2002.
    • (2002)
    • Nagarathnam, D.1    Asgari, D.2    Shao, J.3    Liu, X.-G.4    Khire, U.5    Wang, C.6    Hart, B.7    Boyer, S.8    Weber, O.9    Lynch, M.10    Bankston, D.11
  • 28
    • 79960477531 scopus 로고    scopus 로고
    • See http://www.prosense.net/files/ARSST-4pages.pdf and http://www.fauske.com/Download%5Cchemical%5Carsst%5CJPBArticle.pdf.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.