- Retro-Ene Reactions in Heterocyclic Synthesis. III. A New Route to 4,5-Dihydrooxazoles and 5,6-Dihydro-4H-1,3-oxazines
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Methyl (E)-4,4-dimethyl-5-oxo-2-pentenoate (1, X = O) reacted with 1,2- or 1,3-aminoalcohols 3 to yield oxazolidines 4a-c or tetrahydro-1,3-oxazines 4d,e. The corresponding imino ester 1 (X = NBu-t) also gave 4 on reaction with 3. Compounds 4 on heating at 230° yielded 4,5-dihydrooxazoles 5a-c or 5,6-dihydro-4H-1,3-oxazines 5d,e along with methyl 4-methyl-3-pentenoale (6).
- Ito, Kunio,Miyajima, Shingo
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- Pictet-Spengler reaction: Is carbonyl the best choice? A highly diastereoselective alternative approach to trans-1,3-disubstituted tetrahydro-β-carbolines
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Unprecedented 1,2,3-trisubstituted tetrahydro-β-carbolines (THBCs) have been synthesized via a short and highly diastereoselective synthetic route. The key step of the sequence is a flexible variant of the Pictet-Spengler reaction employing synthetic equivalents of several non-available carbonyl compounds. Using one such synthon, the resultant THBC could be further ring- closed to a tetracyclic indole alkaloidal skeleton. (C) 2000 Elsevier Science Ltd.
- Singh, Kamaljit,Deb, Prasant K.
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p. 4977 - 4980
(2007/10/03)
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- SYNTHESIS OF ISOTHIOCYANATES FROM NON-AROMATIC NITROGEN-CONTAINING HETEROCYCLES
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Investigation of the reaction of thiophosgene with Δ2-oxazolines I, Δ3-thiazolines II, 4H-benzothiazines III, 2-methoxypentahydro-Δ1-azepine IV, theophylline and caffeine showed that only compounds I and IV reacted to give 2-acyloxyethyl isothiocyanates and methyl 6-isothiocyanatohexanoate.The structure of these products was corroborated by IR, 1H NMR, 13C NMR and mass spectral methods.The suitability of the above-mentioned compounds to react is discussed.
- Gonda, Jozef,Kristian, Pavol,Mikler, Lubomir
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p. 112 - 117
(2007/10/02)
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