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Volumn 72, Issue 41, 2016, Pages 6455-6466

A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form

Author keywords

Amino azaindole; N Alkylation; Reductive cyclization; Synthesis; Tautomers

Indexed keywords

DIETHYL 2 (2 AMINO 3 NITROPYRIDIN 4 YL)MALONATE; DIETHYL 2 (2 AMINO 5 NITROPYRIDIN 4 YL)MALONATE; ETHYL 5 AMINO 2 HYDROXY 1H PYRROLO[2,3 C]PYRIDINE 3 CARBOXYLATE; ETHYL 7 AMINO 1 BENZYL 2 HYDROXY 1H PYRROLO[2,3 C]PYRIDINE 3 CARBOXYLATE; ETHYL 7 AMINO 2 HYDROXY 1 (2 OXO 2 PHENETHYLAMINO)ETHYL 1H PYRROLO[2,3 C]PYRIDINE 3 CARBOXYLATE; ETHYL 7 AMINO 2 HYDROXY 1 (2 OXO 2 PHENETHYLAMINO)ETHYL 1H PYRROLO[2,3 C]PYRIDINE 3 CARBOXYLATE HYDROCHLORIDE; ETHYL 7 AMINO 2 HYDROXY 1 METHYL 1H PYRROLO[2,3 C]PYRIDINE 3 CARBOXYLATE; ETHYL 7 AMINO 2 HYDROXY 1H PYRROLO[2,3 C]PYRIDINE 3 CARBOXYLATE; ETHYL 7 AMINO 2 HYDROXY 1H PYRROLO[2,3 C]]PYRIDINE 3 CARBOXYLATE HYDROCHLORIDE; N' (4 CHLORO 3 NITROPYRIDIN 2 YL) N,N DIMETHYLFORM AMIDE; N' (4 CHLORO 5 NITROPYRIDIN 2 YL) N,N DIMETHYLFORM AMIDE; OXINDOLE; PYRROLE; UNCLASSIFIED DRUG;

EID: 84988019819     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2016.08.055     Document Type: Article
Times cited : (5)

References (53)
  • 10
    • 84943388739 scopus 로고
    • A.R. Katritzki C.W. Rees Pergamon Oxford
    • 6 Sundberg, R.J., Katritzki, A.R., Rees, C.W., (eds.) Comprehensive Heterocyclic Chemistry, Vol. 4, 1984, Pergamon, Oxford, 313–376.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 313-376
    • Sundberg, R.J.1
  • 16
    • 85043128749 scopus 로고    scopus 로고
    • T. PCT. Int. Appl. WO2015/013777 A2, 2015; U.S. Patent 14 904 893.
    • 10 Tzvetkov, N. T. PCT. Int. Appl. WO2015/013777 A2, 2015; U.S. Patent 14 904 893, 2016.
    • (2016)
    • Tzvetkov, N.1
  • 34
    • 85043102485 scopus 로고    scopus 로고
    • CCDC 1484697 (18) and CCDC 1484698 (19) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • 23 CCDC 1484697 (18) and CCDC 1484698 (19) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.ac.uk/data_request/cif.
  • 36
    • 85043107584 scopus 로고    scopus 로고
    • Intramolecular reductive cyclization of 3-nitro-substituted pyridine 20 would proceed in a non-selective formation of purine and azaindole derivatives due to the in situ obtained 3-amino function after the reduction step.
    • 25 Intramolecular reductive cyclization of 3-nitro-substituted pyridine 20 would proceed in a non-selective formation of purine and azaindole derivatives due to the in situ obtained 3-amino function after the reduction step.
  • 37
    • 85043127313 scopus 로고    scopus 로고
    • Compound 12a was isolated as a hydrochloride salt under these conditions.
    • 26 Compound 12a was isolated as a hydrochloride salt under these conditions.
  • 43
    • 85043099531 scopus 로고    scopus 로고
    • Ester cleavage of 12a was achieved with lithium hydroxide in methanol-THF solution (1:1) at room temperature.
    • 31 Ester cleavage of 12a was achieved with lithium hydroxide in methanol-THF solution (1:1) at room temperature.
  • 44
    • 85043107393 scopus 로고    scopus 로고
    • Advanced Chemistry Development Toronto, ON, Canada
    • 32 ACD/Percepta, Version 14.0, 2015, Advanced Chemistry Development, Toronto, ON, Canada www.acdlabs.com.
    • (2015) ACD/Percepta, Version 14.0
  • 45
    • 85043106086 scopus 로고    scopus 로고
    • ChemAxon ()
    • 33 Instant JChem 16.4.11.0, 2016 ChemAxon ( http://www.chemaxon.com).
    • (2016) Instant JChem 16.4.11.0
  • 47
    • 85043095264 scopus 로고    scopus 로고
    • Our results indicate that amide coupling reactions of N1-unsubstituted amino-6-azaoxindole derivatives with in situ formed acyl halides, i.e., under acidic conditions may led to a mixture of N1-acetylated and amide-coupled products.
    • 35 Our results indicate that amide coupling reactions of N1-unsubstituted amino-6-azaoxindole derivatives with in situ formed acyl halides, i.e., under acidic conditions may led to a mixture of N1-acetylated and amide-coupled products.
  • 53
    • 84991523669 scopus 로고    scopus 로고
    • Quantum chemical calculation of tautomeric equilibria
    • L. Antonov Wiley-VCH Weinheim
    • 39(b) Fabian, W.M.F., Quantum chemical calculation of tautomeric equilibria. Antonov, L., (eds.) Tautomerism: Methods and Theories, 2014, Wiley-VCH, Weinheim, 337–368.
    • (2014) Tautomerism: Methods and Theories , pp. 337-368
    • Fabian, W.M.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.