Cu-Catalyzed iminative hydroolefination of unactivated alkynes en route to 4-imino-tetrahydropyridines and 4-aminopyridines

作者: Ravi Kumar , Shridhar H. Thorat , Maddi Sridhar Reddy

DOI: 10.1039/C6CC08081B

关键词:

摘要: A general method for synthesizing 4-imino tetrahydropyridine derivatives is achieved, from readily available β-enaminones and sulfonyl azides, which comprises a sequential copper catalyzed ketenimine formation its hitherto inaccessible intramolecular hydrovinylation. The products are shown as ready precursors highly valuable 4-sulfonamidopyridine via DDQ mediated oxidation.

参考文章(49)
Maddi Sridhar Reddy, Yalla Kiran Kumar, Nuligonda Thirupathi, A New Synthesis of γ-Butyrolactones via AuCl3- or Hg(II)-Catalyzed Intramolecular Hydroalkoxylation of 4-Bromo-3-yn-1-ols Organic Letters. ,vol. 14, pp. 824- 827 ,(2012) , 10.1021/OL2033493
Shinji Nara, Rieko Tanaka, Jun Eishima, Mitsunobu Hara, Yuichi Takahashi, Shizuo Otaki, Robert J. Foglesong, Philip F. Hughes, Shelley Turkington, Yutaka Kanda, Discovery and structure-activity relationships of novel piperidine inhibitors of farnesyltransferase. Journal of Medicinal Chemistry. ,vol. 46, pp. 2467- 2473 ,(2003) , 10.1021/JM020522K
Mohammad Movassaghi, Matthew D. Hill, Synthesis of Substituted Pyridine Derivatives via the Ruthenium-Catalyzed Cycloisomerization of 3-Azadienynes Journal of the American Chemical Society. ,vol. 128, pp. 4592- 4593 ,(2006) , 10.1021/JA060626A
Sandro Cacchi, Giancarlo Fabrizi, Eleonora Filisti, N-Propargylic β-Enaminones: Common Intermediates for the Synthesis of Polysubstituted Pyrroles and Pyridines Organic Letters. ,vol. 10, pp. 2629- 2632 ,(2008) , 10.1021/OL800518J
Wafa Gati, Mohamed M. Rammah, Mohamed B. Rammah, François Couty, Gwilherm Evano, De Novo Synthesis of 1,4-Dihydropyridines and Pyridines Journal of the American Chemical Society. ,vol. 134, pp. 9078- 9081 ,(2012) , 10.1021/JA303002A
Jesús A. Varela, Carlos Saá, Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition. Chemical Reviews. ,vol. 103, pp. 3787- 3801 ,(2003) , 10.1021/CR030677F
Nuligonda Thirupathi, Madala Hari Babu, Vikas Dwivedi, Ruchir Kant, Maddi Sridhar Reddy, Palladium-Catalyzed Tandem Intramolecular Oxy/Amino-Palladation/Isocyanide Insertion: Synthesis of α-Benzofuranyl/Indolylacetamides Organic Letters. ,vol. 16, pp. 2908- 2911 ,(2014) , 10.1021/OL501048X
Ping Lu, Yanguang Wang, The thriving chemistry of ketenimines Chemical Society Reviews. ,vol. 41, pp. 5687- 5705 ,(2012) , 10.1039/C2CS35159E
Imhyuck Bae, Hoon Han, Sukbok Chang, Highly Efficient One-Pot Synthesis of N-Sulfonylamidines by Cu-Catalyzed Three-Component Coupling of Sulfonyl Azide, Alkyne, and Amine Journal of the American Chemical Society. ,vol. 127, pp. 2038- 2039 ,(2005) , 10.1021/JA0432968
Muthupandi Nagaraj, Muthusamy Boominathan, Devanathan Perumal, Shanmugam Muthusubramanian, Nattamai Bhuvanesh, Copper(I)-catalyzed cascade sulfonimidate to sulfonamide rearrangement: synthesis of imidazo[1,2-a][1,4]diazepin-7(6H)-one. Journal of Organic Chemistry. ,vol. 77, pp. 6319- 6326 ,(2012) , 10.1021/JO300855F