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Volumn 69, Issue 4, 2004, Pages 1368-1371

N-Amination of Pyrrole and Indole Heterocycles with Monochloramine (N H2Cl)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; AMMONIA; NITROGEN; SUBSTITUTION REACTIONS;

EID: 1242329844     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035587p     Document Type: Article
Times cited : (70)

References (49)
  • 12
    • 0006105631 scopus 로고
    • Hoechst-Roussel Pharmaceuticals Inc.: U.S. Patent 5,459,274, 1995
    • (j) Hoechst-Roussel Pharmaceuticals Inc.: U.S. Patent 5,459,274, 1995; Chem. Abstr. 1995, 124, 145914.
    • (1995) Chem. Abstr. , vol.124 , pp. 145914
  • 25
    • 1242268678 scopus 로고    scopus 로고
    • Unpublished results
    • Hunt, J. Unpublished results.
    • Hunt, J.1
  • 26
    • 1242336213 scopus 로고    scopus 로고
    • note
    • Compound 1 has a reported decomposition onset temperature of 90-110 °C with an energy of 2308 J/g; see ref 1. Subsequent studies in our laboratories confirmed these results, although a lower energy of decomposition was observed: 1269 J/g, onset 105 °C.
  • 27
    • 1242336214 scopus 로고    scopus 로고
    • note
    • 50 = 30 mg/kg.
  • 29
    • 1242291267 scopus 로고    scopus 로고
    • note
    • We have adopted the annotation of Friestad for the compounds in Figure 1; see ref 2.
  • 31
    • 1242268680 scopus 로고    scopus 로고
    • note
    • 2 has given similar results as 1.
  • 38
    • 1242336217 scopus 로고    scopus 로고
    • note
    • Aminopyrrole 3d had significant water solubility contributing to the poor isolated yield due to losses on workup.
  • 39
    • 1242336219 scopus 로고    scopus 로고
    • note
    • a of 2a was determined to be 8.7 ± 0.2 using the spectrophotometric titration method.
  • 40
    • 1242268684 scopus 로고    scopus 로고
    • note
    • Aminoindoles 3i and 31 were noticeably less stable than aminoindoles containing electron-withdrawing groups. Extended reaction times were accompanied with significant degradation of product. This was also observed upon aqueous workup and careful attention was made to exclude oxygen from the workup process.
  • 41
    • 1242336212 scopus 로고    scopus 로고
    • note
    • 2Cl in solution was determined by iodometric titration.
  • 42
    • 1242268682 scopus 로고    scopus 로고
    • note
    • Water content was determined using a Karl Fischer titration instrument.
  • 43
    • 1242268683 scopus 로고    scopus 로고
    • note
    • 4Cl; see ref 16a.
  • 47
    • 1242291266 scopus 로고    scopus 로고
    • 2d: see ref 3i
    • (d) 2d: see ref 3i.
  • 48
    • 1242336210 scopus 로고
    • (e) 2e: prepared by EDCI/HOBt-mediated coupling of n-propylamine with 3-methylpyrrole-2,4-dicarboxylic acid-4-ethyl ester. See: Corwin, A. H.; Viohl, P. J. Am. Chem. Soc. 1944, 66, 1137.
    • (1944) J. Am. Chem. Soc. , vol.66 , pp. 1137
    • Corwin, A.H.1    Viohl, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.