Combinatorial synthetic design. Solution and polymer-supported synthesis of heterocycles via intramolecular aza Diels-Alder and imino alcohol cyclizations

Journal of Combinatorial Chemistry

Volumn 4, Issue 5, 2002, Pages 516-522

  Spaller, Mark R ^a,d   Thielemann, Wolfgang T ^b,d   Brennan, Paul E ^c,d   Bartlett, Paul A ^d  

^a WAYNE STATE UNIVERSITY   (United States)

^b BAYER AG   (Germany)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALCOHOLS; COMBINATORIAL CHEMISTRY TECHNIQUES; HETEROCYCLIC COMPOUNDS;

EID: 0036715582     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc020027+     Document Type: Article

References (23)

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15. Related allylic salicylaldehyde ethers have been studied in a number of contexts for intramolecular cycloadditions. In addition to refs 12 and 13, see the following. Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S.; Thianpatanagul, S.; Kanajun, S. J. Chem. Soc., Chem. Commun. 1986, 602-604. Grigg, R.; Duffy, L. M.; Dorrity, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213-2230. Tietze, L. F. Chem. Rev. 1996, 96, 115-136. Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086.
16. Related allylic salicylaldehyde ethers have been studied in a number of contexts for intramolecular cycloadditions. In addition to refs 12 and 13, see the following. Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S.; Thianpatanagul, S.; Kanajun, S. J. Chem. Soc., Chem. Commun. 1986, 602-604. Grigg, R.; Duffy, L. M.; Dorrity, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213-2230. Tietze, L. F. Chem. Rev. 1996, 96, 115-136. Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086.
17. Related allylic salicylaldehyde ethers have been studied in a number of contexts for intramolecular cycloadditions. In addition to refs 12 and 13, see the following. Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S.; Thianpatanagul, S.; Kanajun, S. J. Chem. Soc., Chem. Commun. 1986, 602-604. Grigg, R.; Duffy, L. M.; Dorrity, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213-2230. Tietze, L. F. Chem. Rev. 1996, 96, 115-136. Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086.
18. Related allylic salicylaldehyde ethers have been studied in a number of contexts for intramolecular cycloadditions. In addition to refs 12 and 13, see the following. Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S.; Thianpatanagul, S.; Kanajun, S. J. Chem. Soc., Chem. Commun. 1986, 602-604. Grigg, R.; Duffy, L. M.; Dorrity, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213-2230. Tietze, L. F. Chem. Rev. 1996, 96, 115-136. Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086.
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23. A referee has suggested that the acidic conditions for cleavage of the acylated products from resin may facilitate isomerization and conversion of a minor isomer to the thermodynamically favored compound.