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Access via FulcrumSynthesis of the new ring system, Pyrazolo[3,4‐d][1,3]diazepine. A novel route for the synthesis of azolo[1,3]diazepines
| dc.contributor.author | Acevedo, Oscar L. | en_US |
| dc.contributor.author | Krawczyk, Steven H. | en_US |
| dc.contributor.author | Townsend, Leroy B. | en_US |
| dc.date.accessioned | 2013-02-12T19:00:40Z | |
| dc.date.available | 2013-02-12T19:00:40Z | |
| dc.date.issued | 1985-03 | en_US |
| dc.identifier.citation | Acevedo, Oscar L.; Krawczyk, Steven H.; Townsend, Leroy B. (1985). "Synthesis of the new ring system, Pyrazolo[3,4‐d][1,3]diazepine. A novel route for the synthesis of azolo[1,3]diazepines." Journal of Heterocyclic Chemistry 22(2): 349-352. <http://hdl.handle.net/2027.42/96300> | en_US |
| dc.identifier.issn | 0022-152X | en_US |
| dc.identifier.issn | 1943-5193 | en_US |
| dc.identifier.uri | https://hdl.handle.net/2027.42/96300 | |
| dc.description.abstract | A reduction of the nitrile group of 5‐amino‐4‐cyano‐1‐methylpyrazole ( 3 ) has provided the very versatile compound 5‐amino‐1‐methylpyrazole‐4‐carboxaldehyde ( 4 ). The amino group of 4 was protected using di‐methylformamide dimethylacetal and the aldehyde group was then reacted with trimethylsilyl cyanide to afford the moisture sensitive compound 5‐[[(dimethylamino)methylene]amino]‐4‐[cyano(trimethylsiloxy)‐methyl]‐1‐methylpyrazole ( 10 ). The cyano group of the cyanohydrin 10 was reduced using a cobalt boride catalyst to afford an intermediate aminomethyl group which was involved in an in situ annulation. This reaction provided 1‐methyl‐1,4,5,6‐tetrahydropyrazolo[3,4‐ d ][1,3]diazepin‐4‐ol, a derivative of the new ring system, pyrazolo[3,4‐ d ][1,3]diazepine. | en_US |
| dc.publisher | Wiley‐Blackwell | en_US |
| dc.title | Synthesis of the new ring system, Pyrazolo[3,4‐d][1,3]diazepine. A novel route for the synthesis of azolo[1,3]diazepines | en_US |
| dc.type | Article | en_US |
| dc.rights.robots | IndexNoFollow | en_US |
| dc.subject.hlbsecondlevel | Organic Chemistry | en_US |
| dc.subject.hlbtoplevel | Science | en_US |
| dc.description.peerreviewed | Peer Reviewed | en_US |
| dc.contributor.affiliationum | Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109‐1065 | en_US |
| dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/96300/1/5570220225_ftp.pdf | |
| dc.identifier.doi | 10.1002/jhet.5570220225 | en_US |
| dc.identifier.source | Journal of Heterocyclic Chemistry | en_US |
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| dc.identifier.citedreference | Reaction of the ortho ‐amino aldehyde 4 with dimethylform‐amide dimethylacetal gave excellent yields of the corresponding [(dimethylamino)methylene]amino product, compound 8. However, the product contained a small amount of the [(methoxy)methylene]amino product, compound 9. When these compounds were separated on silica gel, compounds 8 and 9 were shown to give different and distinct trimethylsilyl cyanohydrins 10 and 11, respectively. Compounds 10 and 11 were in turn hydrogenated to afford an identical mixture of compounds 13 and 7, in each case. | en_US |
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| dc.identifier.citedreference | The cobalt boride catalyst was prepared in an analogous manner with the nickel boride catalyst, by a reduction of COCl 2 6H 2 O with sodium borohydride in water. The black flocculent precipitates which were formed from the reductions are washed with water and stored under absolute ethanol: H. C. Brown and C. A. Brown, Tetrahedron, Suppl. No. 8,Part 1, 149 ( 1966 ); H. C. Brown and C. A. Brown, Chem. Abstr., 68, 68529p ( 1968 ). | en_US |
| dc.identifier.citedreference | A preliminary account of this work was presented at the Ninth International Congress of Heterocyclic Chemistry, Tokyo, Japan, August 1983; L. B. Townsend, S. H. Krawczyk and O. L. Acevedo,Abstract No. P‐229 and O. L. Acevedo, S. H. Krawczyk and L. B. Townsend, Tetrahedron Letters, 4789 ( 1983 ). | en_US |
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| dc.identifier.citedreference | This investigation was supported by grant number CA‐28381 awarded by the National Cancer Institute D.H.E.W., and the U.N.D.P./‐World Bank/W.H.O. Special Program for Research and Training in Tropical Diseases and the Scientific Working Group on Filariasis (800134). | en_US |
| dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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