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Volumn 73, Issue 6, 2008, Pages 2285-2291

Synthetic utilization of polynitroaromatic compounds. 6. Remarkable regioselectivity in nucleophilic displacement of aromatic nitro groups with amines

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; HYDROGEN BONDS; NUCLEOPHILES; REGIOSELECTIVITY;

EID: 41849114948     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702532x     Document Type: Article
Times cited : (18)

References (33)
  • 28
    • 34447286020 scopus 로고    scopus 로고
    • The absence of a carbonyl group could favor peri-substitution by decreasing the steric hindrance in particular, this factor could be essential for annulated six- and seven-membered heterocycles, Thus, the latest data show that reaction of 3-acetyl-2-methyl-5,7-dinitroquinoline with PhSH results in selective peri-substitution: Mezhnev, V. V, Dutov, M. D, Sapozhnikov, O. Yu, Kachala, V. V, Shevelev, S. A. Mendeleev Commun. 2007, 234. For more detailed discussion, see Supporting Information
    • The absence of a carbonyl group could favor peri-substitution by decreasing the steric hindrance (in particular, this factor could be essential for annulated six- and seven-membered heterocycles). Thus, the latest data show that reaction of 3-acetyl-2-methyl-5,7-dinitroquinoline with PhSH results in selective peri-substitution: Mezhnev, V. V.; Dutov, M. D.; Sapozhnikov, O. Yu.; Kachala, V. V.; Shevelev, S. A. Mendeleev Commun. 2007, 234. For more detailed discussion, see Supporting Information.
  • 31
    • 0005044905 scopus 로고
    • Wiley & Sons: New York, Collect
    • (a) Organic Syntheses; Wiley & Sons: New York, 1941; Collect. Vol. I, p 541.
    • (1941) Organic Syntheses , vol.1 , pp. 541
  • 32
    • 84878920897 scopus 로고
    • Wiley & Sons: New York, Collect
    • (b) Organic Syntheses; Wiley & Sons: New York, 1941; Collect. Vol. I, p 455.
    • (1941) Organic Syntheses , vol.1 , pp. 455
  • 33
    • 1442359950 scopus 로고    scopus 로고
    • In the 1H NMR spectrum of 3, signals of 2-acetylamino-4,6-dinitrobenzoic acid are present, evidently due to hydrolysis of 3 in water-containing DMSO-d6. This instability of 2-methylbenz[d][1,3]oxazine-4-ones (which leads, in particular, to the problems with NMR spectra interpretation) is well known: Rocco, S. A, Barbarini, J. E, Rittner, R. Synthesis 2004, 429 and references cited therein
    • 6. This instability of 2-methylbenz[d][1,3]oxazine-4-ones (which leads, in particular, to the problems with NMR spectra interpretation) is well known: Rocco, S. A.; Barbarini, J. E.; Rittner, R. Synthesis 2004, 429 and references cited therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.