Abstract
The one-step reaction of some amino-substituted heterocycles with diiodomethane to give azacyanines is reported. This useful reaction is of wider application than initially reported and includes the synthesis of new substituted pyrido-, isoquino-, benzimadazo-, and benzothiazoazacyanines 7. Furthermore, treatment of these azacyanines with base generally affects a facile opening of the dihydrotriazinium ring resulting in the formation of new heterocycles 10, 11, and 12, which would be difficult to prepare by other means. This reaction takes an additional direction in the case of halo-substituted azacyanines 7b/c/d where treatment with base gives rise to new interesting derivatives of dipyridotriazines 14b/c/d.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1310-1315 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 66 |
| Issue number | 4 |
| DOIs | |
| State | Published - Feb 23 2001 |
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ASJC Scopus subject areas
- Organic Chemistry
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Synthesis and reactions of some heterocyclic azacyanines. / Huang, K. S.; Haddadin, M. J.; Olmstead, M. M.; Kurth, M. J.
In: Journal of Organic Chemistry, Vol. 66, No. 4, 23.02.2001, p. 1310-1315.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and reactions of some heterocyclic azacyanines
AU - Huang, K. S.
AU - Haddadin, M. J.
AU - Olmstead, M. M.
AU - Kurth, M. J.
PY - 2001/2/23
Y1 - 2001/2/23
N2 - The one-step reaction of some amino-substituted heterocycles with diiodomethane to give azacyanines is reported. This useful reaction is of wider application than initially reported and includes the synthesis of new substituted pyrido-, isoquino-, benzimadazo-, and benzothiazoazacyanines 7. Furthermore, treatment of these azacyanines with base generally affects a facile opening of the dihydrotriazinium ring resulting in the formation of new heterocycles 10, 11, and 12, which would be difficult to prepare by other means. This reaction takes an additional direction in the case of halo-substituted azacyanines 7b/c/d where treatment with base gives rise to new interesting derivatives of dipyridotriazines 14b/c/d.
AB - The one-step reaction of some amino-substituted heterocycles with diiodomethane to give azacyanines is reported. This useful reaction is of wider application than initially reported and includes the synthesis of new substituted pyrido-, isoquino-, benzimadazo-, and benzothiazoazacyanines 7. Furthermore, treatment of these azacyanines with base generally affects a facile opening of the dihydrotriazinium ring resulting in the formation of new heterocycles 10, 11, and 12, which would be difficult to prepare by other means. This reaction takes an additional direction in the case of halo-substituted azacyanines 7b/c/d where treatment with base gives rise to new interesting derivatives of dipyridotriazines 14b/c/d.
UR - http://www.scopus.com/inward/record.url?scp=0035936786&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0035936786&partnerID=8YFLogxK
U2 - 10.1021/jo001484k
DO - 10.1021/jo001484k
M3 - Article
C2 - 11312961
AN - SCOPUS:0035936786
VL - 66
SP - 1310
EP - 1315
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 4
ER -