Desilylative activation of TMSCN in chemoselective Strecker-Ugi type reaction: functional fused imidazoles as building blocks as an entry route to annulated purines

被引：27

作者：

Guchhait, Sankar K. ^{[1
]}

Chaudhary, Vikas ^{[1
]}

机构：

[1] NIPER, Dept Med Chem, Mohali 160062, Punjab, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 34期

关键词：

ADENOSINE RECEPTOR ANTAGONISTS; ONE-POT; DERIVATIVES; INHIBITORS; WATER; GENERATION; BASE; ACID;

D O I：

10.1039/c4ob00882k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A pathway of desilylative activation of TMSCN as a functional isonitrile equivalent, and DABCO-THF as an appropriate system for activation in a chemoselective Strecker-Ugi type reaction, has rendered ethyl glyoxalate and various heterocyclic-2-amidines as feasible substrates, and afforded the successful synthesis of 3-amino-2-carboxyethyl substituted fused imidazoles as useful building blocks. This class of functional scaffold has provided, via construction of the fused pyrimidinone motif, the synthesis of biologically important C8-N9 annulated purines, adenines and their oxo/thio analogs. This new approach is convenient and flexible for the preparation of versatile purine-condensed heterocycles.

引用

页码：6694 / 6705

页数：12

共 37 条

[1] A novel class of orally active non-peptide bradykinin B2 receptor antagonists.: 1.: Construction of the basic framework [J].

Abe, Y ;

Kayakiri, H ;

Satoh, S ;

Inoue, T ;

Sawada, Y ;

Imai, K ;

Inamura, N ;

Asano, M ;

Hatori, C ;

Katayama, A ;

Oku, T ;

Tanaka, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (04) :564-578

[2] Potent tetracyclic guanine inhibitors of PDE1 and PDE5 cyclic guanosine monophosphate phosphodiesterases with oral antihypertensive activity [J].

Ahn, HS ;

Bercovici, A ;

Boykow, G ;

Bronnenkant, A ;

Chackalamannil, S ;

Chow, J ;

Cleven, R ;

Cook, J ;

Czarniecki, M ;

Domalski, C ;

Fawzi, A ;

Green, M ;

Gundes, A ;

Ho, G ;

Laudicina, M ;

Lindo, N ;

Ma, K ;

Manna, M ;

McKittrick, B ;

Mirzai, B ;

Nechuta, T ;

Neustadt, B ;

Puchalski, C ;

Pula, K ;

Silverman, L ;

Smith, E ;

Stamford, A ;

Tedesco, RP ;

Tsai, HG ;

Tulshian, D ;

Vaccaro, H ;

Watkins, RW ;

Weng, XY ;

Witkowski, JT ;

Xia, Y ;

Zhang, HT .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (14) :2196-2210

[3] New pyrrolo[2,1-f]purine-2,4-dione and imidazo[2,1-f]purine-2,4-dione derivatives as potent and selective human A3 adenosine receptor antagonists [J].

Baraldi, PG ;

Preti, D ;

Tabrizi, MA ;

Fruttarolo, F ;

Romagnoli, R ;

Zaid, NA ;

Moorman, AR ;

Merighi, S ;

Varani, K ;

Borea, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (14) :4697-4701

[4] An efficient one-pot synthesis of 6-alkoxy-8,9-dialkylpurines via reaction of 5-amino-4-chloro-6-alkylaminopyrimidines with N,N-dimethylalkaneamides and alkoxide ions [J].

Baraldi, PG ;

Broceta, AU ;

de las Infantas, MJP ;

Mochun, JJD ;

Espinosa, A ;

Romagnoli, R .

TETRAHEDRON, 2002, 58 (38) :7607-7611

[5] N-Fused Imidazoles As Novel Anticancer Agents That Inhibit Catalytic Activity of Topoisomerase IIα and Induce Apoptosis in G1/S Phase [J].

Baviskar, Ashish T. ;

Madaan, Chetna ;

Preet, Ranjan ;

Mohapatra, Purusottam ;

Jain, Vaibhav ;

Agarwal, Amit ;

Guchhait, Sankar K. ;

Kundu, Chanakya N. ;

Banerjee, Uttam C. ;

Bharatam, Prasad V. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (14) :5013-5030

[6] ANTIINFLAMMATORY ACTIVITY OF SUBSTITUTED 6-HYDROXYPYRIMIDO[2,1-F]PURINE-2,4,8(1H,3H,9H)-TRIONES - ATYPICAL NONSTEROIDAL ANTIINFLAMMATORY AGENTS [J].

BLYTHIN, DJ ;

KAMINSKI, JJ ;

DOMALSKI, MS ;

SPITLER, J ;

SOLOMON, DM ;

CONN, DJ ;

WONG, SC ;

VERBIAR, LL ;

BOBER, LA ;

CHIU, PJS ;

WATNICK, AS ;

SIEGEL, MI ;

HILBERT, JM ;

MCPHAIL, AT .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) :1099-1113

[7] Intramolecular Direct C-H Arylation Approach to Fused Purines. Synthesis of Purino[8,9-f]phenanthridines and 5,6-Dihydropurino[8,9-a]isoquinolines [J].

Cerna, Igor ;

Pohl, Radek ;

Klepetarova, Blanka ;

Hocek, Michal .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (07) :2302-2308

[8] Rapid synthesis of 3-amino-imidazopyridines by a microwave-assisted four-component coupling in one pot [J].

DiMauro, Erin F. ;

Kennedy, Joseph M. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :1013-1016

[9] Imidazo[1,2-a]pyrimidines as functionally selective and orally bioavailable GABA-α2/α3 binding site agonists for the treatment of anxiety disorders [J].

Goodacre, SC ;

Street, LJ ;

Hallett, DJ ;

Crawforth, JM ;

Kelly, S ;

Owens, AP ;

Blackaby, WP ;

Lewis, RT ;

Stanley, J ;

Smith, AJ ;

Ferris, P ;

Sohal, B ;

Cook, SM ;

Pike, A ;

Brown, N ;

Wafford, KA ;

Marshall, G ;

Castro, JL ;

Atack, JR .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (01) :35-38

[10] Discovery of 1-[9-(4-Chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-4-ethylaminopiperidine-4-carboxylic Acid Amide Hydrochloride (CP-945,598), a Novel, Potent, and Selective Cannabinoid Type 1 Receptor Antagonist [J].

Griffith, David A. ;

Hadcock, John R. ;

Black, Shawn C. ;

Iredale, Philip A. ;

Carpino, Philip A. ;

DaSilva-Jardine, Paul ;

Day, Robert ;

DiBrino, Joseph ;

Dow, Robert L. ;

Landis, Margaret S. ;

O'Connor, Rebecca E. ;

Scott, Dennis O. .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (02) :234-237

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