An Efficient Solid-phase Parallel Synthesis of 2-Amino and 2-Amidobenzo[d]oxazole Derivatives via Cyclization Reactions of 2-Hydroxyphenylthiourea Resin 


Vol. 33,  No. 12, pp. 4109-4116, Dec.  2012
10.5012/bkcs.2012.33.12.4109


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  Abstract

An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]- oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo- [d]oxazole resins 4 by cyclization reaction of 2-hydroxyphenylthiourea resin 3. The resin-bound 2-hydroxyphenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2- amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane (CH2Cl2).

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  Cite this article

[IEEE Style]

S. Jung, S. Kim, G. Lee, Y. Gong, "An Efficient Solid-phase Parallel Synthesis of 2-Amino and 2-Amidobenzo[d]oxazole Derivatives via Cyclization Reactions of 2-Hydroxyphenylthiourea Resin," Bulletin of the Korean Chemical Society, vol. 33, no. 12, pp. 4109-4116, 2012. DOI: 10.5012/bkcs.2012.33.12.4109.

[ACM Style]

Se-Lin Jung, Seul-Gi Kim, Gee-Hyung Lee, and Young-Dae Gong. 2012. An Efficient Solid-phase Parallel Synthesis of 2-Amino and 2-Amidobenzo[d]oxazole Derivatives via Cyclization Reactions of 2-Hydroxyphenylthiourea Resin. Bulletin of the Korean Chemical Society, 33, 12, (2012), 4109-4116. DOI: 10.5012/bkcs.2012.33.12.4109.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949