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Volumn 70, Issue 16, 2005, Pages 6230-6241

Synthesis of 3-substituted bicyclic imidazo[1,2-d][1,2,4]thiadiazoles and tricyclic benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazoles

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; CRYSTAL STRUCTURE; ESTERS; NITRILE RESINS; ORGANIC COMPOUNDS; REACTION KINETICS; SCAFFOLDS; SUBSTITUTION REACTIONS;

EID: 23044459107     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0507486     Document Type: Article
Times cited : (33)

References (51)
  • 4
    • 33544454880 scopus 로고    scopus 로고
    • note
    • The CAS Registry No. for terrazole is 25-931-59.
  • 15
    • 77956780168 scopus 로고    scopus 로고
    • Bristol, J. A., Ed.; Academic Press: London, Chapter 34
    • Cheng, X.-M. Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press: London, 1996; Vol. 31, Chapter 34, pp 337-355; in particular p 339.
    • (1996) Annual Reports in Medicinal Chemistry , vol.31 , pp. 337-355
    • Cheng, X.-M.1
  • 20
    • 0036259879 scopus 로고    scopus 로고
    • For a review on inhibitors targeting the cysteine residues of biomolecules, see the following: Scozzafava, A.; Casini, A.; Supuran, C. T. Curr. Med. Chem. 2002, 9, 1167-1185.
    • (2002) Curr. Med. Chem. , vol.9 , pp. 1167-1185
    • Scozzafava, A.1    Casini, A.2    Supuran, C.T.3
  • 43
    • 33544469101 scopus 로고    scopus 로고
    • note
    • Other isocyanates (methyl, ethyl, propyl) work equally well. However, we settled for n-butyl isocyanate because of cost and safety (higher bp) considerations and commercial availability in kilogram quantity.
  • 44
    • 33544473735 scopus 로고
    • Noland, W. E., Ed; John Wiley & Sons, Inc.: Toronto; Collect. Vol.
    • For a preparative procedure for p-TsCN, see the following, Vrijland, M. S. A. In Organic Syntheses; Noland, W. E., Ed; John Wiley & Sons, Inc.: Toronto, 1988; Collect. Vol. VI, pp 727-730.
    • (1988) Organic Syntheses , vol.6 , pp. 727-730
    • Vrijland, M.S.A.1
  • 45
    • 33544459165 scopus 로고    scopus 로고
    • note
    • We do not have a reasonable explanation for this observation. However, we also noted that 1,3-, 1,4-, and 1,6-alkyldiamines are available reasonably cheaply in kg's quantities from commercial suppliers, but 1,5-diaminopentane is supplied in small quantities (25 g bottle) and is relatively much more expensive.
  • 46
    • 33544461759 scopus 로고    scopus 로고
    • note
    • +) and that of N2 was 10.72 (NH).
  • 48
    • 33544461469 scopus 로고    scopus 로고
    • note
    • Based on the experimental design (monitoring of 2-mercaptobenzimidazole), we cannot preclude the formation of an imine type intermediate like 28a or 28b in the case of 7f. However, in a different system and different conditions, the intermediates shown below were isolated (see ref 18c): (Diagram presented)
  • 49
    • 33544457890 scopus 로고    scopus 로고
    • note
    • A major part of this work has been the subject of US patent 5,677,302, 1997 (ref 17b) and US patent application 20030225007A1, 2003 (ref 18c).
  • 51
    • 0037031631 scopus 로고    scopus 로고
    • 2 and its associated J value (≈ 6 Hz), see: Grehn, L.; Ragnarsson, U. J. Org. Chem. 2002, 67, 6557-6559.
    • (2002) J. Org. Chem. , vol.67 , pp. 6557-6559
    • Grehn, L.1    Ragnarsson, U.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.