Abstract
This protocol describes a rapid, high-yielding, microwave-mediated route that affords benzazole heterocycles in high crude purity and represents a significant advancement toward an environmentally friendly reaction. The reaction of aryl isothiocyanates with o-nucleophilic anilines produces thiourea intermediates that, in the presence of a carbodiimide-functionalized resin, cyclize to benzazoles with the safe removal of one equivalent of hydrogen sulfide. This procedure takes ĝ̂1/48.5 h to complete: 1g-3 h for setup, 4.5 h for benzazole formation and 2 h for workup and purification.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1731-1736 |
| Number of pages | 6 |
| Journal | Nature Protocols |
| Volume | 5 |
| Issue number | 11 |
| DOIs | |
| State | Published - Oct 2010 |
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ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
Cite this
A rapid and efficient route to benzazole heterocycles. / Carpenter, Richard D.; Kurth, Mark J.
In: Nature Protocols, Vol. 5, No. 11, 10.2010, p. 1731-1736.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A rapid and efficient route to benzazole heterocycles
AU - Carpenter, Richard D.
AU - Kurth, Mark J.
PY - 2010/10
Y1 - 2010/10
N2 - This protocol describes a rapid, high-yielding, microwave-mediated route that affords benzazole heterocycles in high crude purity and represents a significant advancement toward an environmentally friendly reaction. The reaction of aryl isothiocyanates with o-nucleophilic anilines produces thiourea intermediates that, in the presence of a carbodiimide-functionalized resin, cyclize to benzazoles with the safe removal of one equivalent of hydrogen sulfide. This procedure takes ĝ̂1/48.5 h to complete: 1g-3 h for setup, 4.5 h for benzazole formation and 2 h for workup and purification.
AB - This protocol describes a rapid, high-yielding, microwave-mediated route that affords benzazole heterocycles in high crude purity and represents a significant advancement toward an environmentally friendly reaction. The reaction of aryl isothiocyanates with o-nucleophilic anilines produces thiourea intermediates that, in the presence of a carbodiimide-functionalized resin, cyclize to benzazoles with the safe removal of one equivalent of hydrogen sulfide. This procedure takes ĝ̂1/48.5 h to complete: 1g-3 h for setup, 4.5 h for benzazole formation and 2 h for workup and purification.
UR - http://www.scopus.com/inward/record.url?scp=78049410391&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=78049410391&partnerID=8YFLogxK
U2 - 10.1038/nprot.2010.132
DO - 10.1038/nprot.2010.132
M3 - Article
C2 - 21030949
AN - SCOPUS:78049410391
VL - 5
SP - 1731
EP - 1736
JO - Nature Protocols
JF - Nature Protocols
SN - 1754-2189
IS - 11
ER -