Addition of some aminoheterocycles to N-benzyl-3-cyanopyridinium chloride

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 391-394

  Volochnyuk, Dmitriy M ^a   Kostyuk, Alexandr N ^a   Pinchuk, Alexandr M ^a   Tolmachev, Andrei A ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

1,4 dihydropyridine; Aminoheterocycles; Nucleophilic addition; Pyridinium salts

Indexed keywords

2 AMINOTHIAIZOLE; 5 AMINOTHIOISOXAZOLE; 6 AMINOURACIL; HETEROCYCLIC AMINE; N BENZYL 3 CYANOPYRIDINIUM CHLORIDE; PYRAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037420992     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02508-X     Document Type: Article

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30. Typical procedure: To a solution of N-benzyl-3-cyanopyridinium chloride 1 and 2 mmol of triethylamine in DMSO 3 mL was added a solution of 6-aminouracil 6 in DMSO 5 mL. The reaction mixture was maintained under argon at 4°C for 12 h, and then poured into 50 mL of water. The precipitated solid was collected by filtration and recrystallized from acetonitrile.
31. 2H), 7.30-7.40 (5H, m, Ph).
32. 2Ph), 79.6 (C(3)), 89.3 (C(5′, ur.)), 103.4 (C(5)), 120.2 (CN), 127.1 (C(o-Ph)), 127.3 (C(p-Ph)), 128.4 (C(m-Ph)), 128.6 (C(6)), 137.1 (C(ipso-Ph)), 143.3 (C(2)), 150.5 (C(6′, ur.)), 152.4 (C(4′, ur.)), 160.6 (C(2′, ur.)).
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36. +, 18), 445 (24), 392 (23), 91 (100).