Synthesis of polycyclic nitrogen-contaning heterocycles: One pot formation of 1,6-naphthyridine ring system by reaction of amino-cycano-methyl thioheterocycles with dialkyl acetylenedicarboxylates

Heterocycles

Volumn 42, Issue 1, 1996, Pages 53-56

  Tominaga, Yoshinori ^a   Yoshioka, Noriko ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002868346     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S13     Document Type: Article

References (34)

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24. ++1).
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26. ++1).
27. +, 4), 496(3), 425(5), 354(5), 277(5), 44(100).
28. Compounds (1d) and (1e) were produced by reaction of 5-nitromethyl-3-phenylpyrazoles with bis(methylthio)-methylenepropanedinitrile in the presence of potassium carbonate in DMSO in 87 and 91% yields, respectively. Similarly, compounds (1f) and (1g) were also prepared by reaction of the corresponding 3-aminotriazole and 3-methyl-5- aminopyrazole with bis(methylthio)methylenepropanedinitrile.
29. +, 3), 529(100), 515(36), 498(41), 483(57), 419(26), 413(54).
30. 2f: mp 270°C(decomp.). orange needles. Mas: m/z 653(M+,3), 652(6), 651(M+,7), 632(19), 620(50), 45(100).
31. +, 16), 411(4), 384(18), 321(8), 268(7), 45(100).
32. +, 30), 354(21), 353(14), 282(24), 45(100).
33. +, 73), 423(100), 307(32), 279(21), 45(12).
34. An N-H group in 2a and 2b is clealy shown in ir and nmr spectra, while N-H group in compounds (2c-2i) are not fixed by any particular nitrogen atom. In the present paper, we are drawing by tentative assigment of configuration to the N-H group in Table 1.