Efficient syntheses of 5-aminoalkyl-1H-tetrazoles and of polyamines incorporating tetrazole rings

被引:36
作者
Athanassopoulos, CM [1 ]
Garnelis, T [1 ]
Vahliotis, D [1 ]
Papaioannou, D [1 ]
机构
[1] Univ Patras, Dept Chem, GR-26500 Patras, Greece
关键词
D O I
10.1021/ol0477069
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Linear N-omega-tritylated omega-amino th iobenzylam ides and N-alpha,N-omega-ditritylated polyamino mono- or bisthioamides were efficiently converted to the corresponding tetrazole derivatives upon treatment with azidotrimethylsilane under Mitsunobu reaction conditions.
引用
收藏
页码:561 / 564
页数:4
相关论文
共 18 条
[1]   Efficient guanylation of Nα,Nω-difunctionalized polyamines at the secondary amino functions [J].
Athanassopoulos, CM ;
Garnelis, T ;
Pantazaka, E ;
Papaioannou, D .
TETRAHEDRON LETTERS, 2004, 45 (48) :8815-8818
[2]   PRACTICAL SYNTHESIS OF THE PUTATIVE POLYAMINE SPIDER TOXIN FTX - A PROPOSED BLOCKER OF VOLTAGE-SENSITIVE CALCIUM CHANNELS [J].
BLAGBROUGH, IS ;
MOYA, E .
TETRAHEDRON LETTERS, 1994, 35 (13) :2057-2060
[3]   Microwave-assisted synthesis of sterically hindered 3-(5-tetrazolyl)pyridines [J].
Bliznets, IV ;
Vasil'ev, AA ;
Shorshnev, SV ;
Stepanov, AE ;
Lukyanov, SM .
TETRAHEDRON LETTERS, 2004, 45 (12) :2571-2573
[4]   Inhibition of glutathione S-transferase in rat hepatocytes by a glycine-tetrazole modified S-alkyl-GSH analogue [J].
Burg, D ;
Hameetman, L ;
Filippov, DV ;
van der Marel, GA ;
Mulder, GJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (12) :1579-1582
[5]   Potent and selective non-peptidic inhibitors of endothelin-converting enzyme-1 with sustained duration of action [J].
De Lombaert, S ;
Blanchard, L ;
Stamford, LB ;
Tan, J ;
Wallace, EM ;
Satoh, Y ;
Fitt, J ;
Hoyer, D ;
Simonsbergen, D ;
Moliterni, J ;
Marcopoulos, N ;
Savage, P ;
Chou, M ;
Trapani, AJ ;
Jeng, AY .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (03) :488-504
[6]  
DELOMBAERT S, 1995, BIOORG MED CHEM LETT, V5, P145
[7]   An expedient route to the tetrazole analogues of α-amino acids [J].
Demko, ZP ;
Sharpless, KB .
ORGANIC LETTERS, 2002, 4 (15) :2525-2527
[8]   3 SYNTHETIC ROUTES TO A STERICALLY HINDERED TETRAZOLE - A NEW ONE-STEP MILD CONVERSION OF AN AMIDE INTO A TETRAZOLE [J].
DUNCIA, JV ;
PIERCE, ME ;
SANTELLA, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2395-2400
[9]   5-substituted-1H-tetrazoles as carboxylic acid isosteres:: Medicinal chemistry and synthetic methods [J].
Herr, RJ .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) :3379-3393
[10]   Simple fragment syntheses of all four isomers of the spermine alkaloid kukoamine [J].
Karigiannis, G ;
Mamos, P ;
Balayiannis, G ;
Katsoulis, I ;
Papaioannou, D .
TETRAHEDRON LETTERS, 1998, 39 (28) :5117-5120