Synthesis and properties of heterofulvenes. Derivatives of 2,6-dimethyl-.gamma.-pyrone, -.gamma.-thiapyrone, and N-butyl-2,6-dimethyl-.gamma.-pyridone
Oxygen-, sulfur-, and nitrogen-containing heterofulvenes, derivatives of 2,6-dimethyl- gamma -pyrone (1) and - gamma -thiapyrone (2) and Nbutyl-2,6- dimethyl- gamma -pyridone (3), have been prepared, and their properties are reported. The 0 and S heterocycles were prepared by condensation of 1 and 2, respectively, with active methylene compounds in acetic anhydride. The N heterocycles were obtained from the 0 heterocycles by reaction with butylamine. Side reactions were observed when butylamine reacted with methyl 2,6dimethyl-4H- pyran-4-ylidenenitroacetate (6) and 2,6-dimethyl4H-pyran-4-ylidenenitroacetone (5). A new convenient route to heterofulvenes which bear a single substituent at the exocyclic double bond was developed. Thus, heterofulvenes substituted by an acetyl group at the exocyclic double bond were found to undergo acetyl cleavage, under very mild acidic conditions, resulting in the formation of monosubstituted heterofulvenes. Deuterium exchange reactions in the systems under consideration were studied. The NMR, UV, and IR data of the disubstituted and monosubstituted heterofulvenes are discussed in terms of the heteroatom and the substituents at the exocyclic double bond.
- Research Organization:
- Tel Aviv Univ., Israel
- Sponsoring Organization:
- USDOE
- NSA Number:
- NSA-29-029094
- OSTI ID:
- 4336236
- Journal Information:
- Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 7 Vol. 39; ISSN 0022-3263
- Country of Publication:
- Country unknown/Code not available
- Language:
- English
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