Efficient syntheses of polyannular heterocycles featuring microwave- accelerated Bischler-Napieralski reaction, stereoselective Heck cyclization, and Claisen rearrangement

Synlett

Volumn , Issue 4, 2000, Pages 509-513

  Sánchez Sancho, Francisco ^a   Mann, Enrique ^a   Herradón, Bernardo ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Bischler Napieralski reaction; Claisen rearrangement; Heck reaction; Lawesson reaction; Polyannular heterocyclic compounds

Indexed keywords

HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MICROWAVE RADIATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0342699708     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

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16. 1H NMR evidence, 392 mg, 86% yield), that was used without further purification.
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27. The stereochemistry in the exocyclic double bond in 4 and 5 was assigned on basis to the existence of NOE between the olefmic and H-10 protons in the NOESY spectrum, and latter confirmed by a single-crystal X-ray diffraction analysis of 5 (Sánchez-Sancho, F. Ph. D. Dissertation, Universidad Autonoma, Madrid, 1999).
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29. 20
30. 4); the solvent was removed, and the residue was purified by flash-chromatography to give 5 (12 g, 98% yield) as a white solid. M.p.: 124-7 °C.
31. 4. The reactions were not selective, affording mixtures of products with different oxidation states.
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36. 3 moiety in the NOESY spectrum of (±)-7, and confirmed by single-crystal X-ray diffraction analysis of (±)-7.
37. Molecular modeling studies on derivatives of 7 bearing two peptide chains at the stereogenic centres indicate the existence of inter-chain hydrogen bond, forming β- and γ-turns, depending on the nature of the spacer (Chana, A. unpublished observations).
38. Work is in progress along these lines (Herradón, B.; Bello, P.; Chana, A.; Mann, E.; Sánchez-Sancho, F. unpublished observations).
39. 13C NMR, IR, MS) and analytical data (combustion analysis: C, H, N).