Reactivity of 1-nitronaphthalene and 1,3-dinitronaphthalene with conjugated dienes. An easy access to N-naphthylpyrroles

Tetrahedron Letters

Volumn 44, Issue 14, 2003, Pages 2943-2945

  Paredes, Elisa ^a   Kneeteman, María ^a   Gonzalez Sierra, Manuel ^b   Mancini, Pedro M E ^a  

^a UNIVERSIDAD NACIONAL DEL LITORAL   (Argentina)

^b Universidad Nacional de Rosario   (Argentina)

Author keywords

1,3 dinitronaphthalene; 1 nitronaphthalene; N naphthylpyrrole; Phenanthrene

Indexed keywords

1 NITRONAPHTHALENE; ALKADIENE; NAPHTHALENE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CONJUGATION; DIELS ALDER REACTION; HIGH TEMPERATURE; THERMAL ANALYSIS;

BETULACEAE;

EID: 0037474634     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00423-4     Document Type: Article

References (14)

1. Paredes E., Biolatto B., Kneeteman M., Mancini P. Tetrahedron Lett. 41:2000;8079-8082.
2. Paredes E., Biolatto B., Kneeteman M., Mancini P. Tetrahedron Lett. 43:2002;4601-4603.
3. Biolatto B., Kneeteman M., Paredes E., Mancini P. J. Org. Chem. 66:2001;3906-3912.
4. General procedure: The temperature, the length of reaction and the diene/dienophile ratio are given in Tables 1 and 2 for 1 and 6, respectively. An ampule containing 1.0 mmol of the dienophile and the required amount of diene in 0.5 ml of dry benzene was cooled in liquid nitrogen, sealed and then heated in an oil bath. After the reaction time was completed, it was cooled once more in liquid nitrogen and opened. The solution was evaporated and the residue purified by column chromatography in silica gel using hexane/ethyl acetate mixtures as eluent.
5. -1.
6. Ragaini F., Cenini S., Tollari S., Tummolillo G., Beltrami R. Organometallics. 18:1999;928-942.
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8. Scheiner P., Chapman O.L., Lassila J.D. J. Org. Chem. 34:1969;813-816.
9. As a separate experiment, nitrobenzene was also tested with diene 2b. The expected phenylpyrrole was isolated and tested by mass analysis.
10. McDonald E., Suksamrarn A., Wylie R.D. J. Chem. Soc., Perkin Trans. 1. 1979;1893-1900.
11. 8 indicates that when 2,4-hexadiene reacts with nitrosobenzene, the resultant pyrrole retains the methyl groups at its 2 and 5 positions. According to this, in the case of nitronaphthalene reactions, alkylic chains (but not heterosubstituents) present in positions 1 or 4 of diene would remain in N-naphthylpyrroles.
12. The appearance of 1-aminonaphthalene as a by-product in reactions of nitrosoarenes with different dienes was already reported. See Refs. 6, 7, and 8.
13. Traces of naphthylpyrroles were detected by TLC. A solution of p-methoxybenzaldehyde, acetic acid, ethanol and sulfuric acid (3:1:1:4) develop arylpyrroles as a red pot by heating.
14. Novak B.H., Lash T.D. J. Org. Chem. 63:1998;3998-4910.