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Volumn 68, Issue 6, 2003, Pages 2300-2309

Phase-transfer-catalyzed alkylation of guanidines by alkyl halides under biphasic conditions: A convenient protocol for the synthesis of highly functionalized guanidines

Author keywords

[No Author keywords available]

Indexed keywords

BIPHASIC CONDITIONS;

EID: 0037459670     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0265535     Document Type: Article
Times cited : (73)

References (71)
  • 4
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    • Ellis, G. P., Luscombe, D.K., Eds.; Elsevier Science: New York
    • Greenhill, J. L.; Lue, P. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier Science: New York, 1993; Vol. 30, Chapter 5.
    • (1993) Progress in Medicinal Chemistry , vol.30
    • Greenhill, J.L.1    Lue, P.2
  • 8
    • 0036062223 scopus 로고    scopus 로고
    • There is little consensus in the literature over the use of the terms guanylation and guanidinylation. For a thorough discussion of guanidine terminology as used in the scientific community, see: Jones, J. H. J. Peptide Sci. 2002, 8, 285-287.
    • (2002) J. Peptide Sci. , vol.8 , pp. 285-287
    • Jones, J.H.1
  • 9
    • 0345266210 scopus 로고    scopus 로고
    • note
    • The term guanyl has officially been superseded by the term carbamimidoyl, and this conversion should technically be referred to as a carbamimidoylation; however, this is a rather laborious term and is rarely used in the literature.
  • 31
  • 45
    • 0034223083 scopus 로고    scopus 로고
    • 3 or pyrazole) with primary or secondary amines, although the yields for this type of reaction are generally low and require forcing conditions; see: (a) Pátek, M.; Smrcina, M.; Nakanishi, E.; Izawa, H. J. Comb. Chem. 2000, 2, 370-377.
    • (2000) J. Comb. Chem. , vol.2 , pp. 370-377
    • Pátek, M.1    Smrcina, M.2    Nakanishi, E.3    Izawa, H.4
  • 47
    • 0345266206 scopus 로고    scopus 로고
    • note
    • 2). The terminology outlined in this paper avoids such confusions.
  • 48
    • 0344403242 scopus 로고    scopus 로고
    • note
    • 3-X.
  • 49
    • 0345697804 scopus 로고    scopus 로고
    • note
    • This terminology is different from that proposed by Jones, who does not distinguish between the two reaction types and favors the use of guanidinylation to describe the conversion of an amine to a guanidine (see ref 5).
  • 50
    • 0344403243 scopus 로고    scopus 로고
    • note
    • Unprotected guanidines, which are considerably more nucleophilic than their carbamate-protected counterparts, can be further functionalized under a variety of conditions, including conjugate addition, addition to aldehydes/ketones, and nucleophilic displacement. For some representative examples, see refs 18-20.
  • 59
    • 0035804953 scopus 로고    scopus 로고
    • Other reactions of unprotected guanidines: (a) Overman, L. E.; Wolfe, J. P. J. Org. Chem. 2001, 66, 3167-3175.
    • (2001) J. Org. Chem. , vol.66 , pp. 3167-3175
    • Overman, L.E.1    Wolfe, J.P.2
  • 67
    • 0345266184 scopus 로고    scopus 로고
    • note
    • Characterization of compound 5k was problematic due to rotamers, and it was therefore deprotected to give 6k which was fully characterized.
  • 68
    • 0344403239 scopus 로고    scopus 로고
    • 219th National Meeting of the American Chemical Society, San Francisco CA, March 26-31, 2000; American Chemical Society: Washington, DC; MEDI-230
    • Tomioka, M. Book of Abstracts. 219th National Meeting of the American Chemical Society, San Francisco, CA, March 26-31, 2000; American Chemical Society: Washington, DC, 2000; MEDI-230.
    • (2000) Book of Abstracts
    • Tomioka, M.1
  • 69
    • 0344834767 scopus 로고    scopus 로고
    • Listed prices available from the Aldrich Chemical Co., 2002
    • Listed prices available from the Aldrich Chemical Co., 2002.
  • 70
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    • Starks C. M., Liotta, C., Eds.; Academic Press: New York
    • Phase-Transfer Catalysis: Principles and Techniques; Starks, C. M., Liotta, C., Eds.; Academic Press: New York, 1978; pp 112-125.
    • (1978) Phase-Transfer Catalysis: Principles and Techniques , pp. 112-125


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.