REACTIONS OF 2-AMINOIMIDAZOLES WITH ALDEHYDES - HYDROXYALKYLATION AND CYCLOADDITION

被引:17
作者
XU, YZ [1 ]
YAKUSHIJIN, K [1 ]
HORNE, DA [1 ]
机构
[1] COLUMBIA UNIV,DEPT CHEM,NEW YORK,NY 10027
关键词
D O I
10.1016/S0040-4039(00)61576-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction between 2-aminoimidazoles and aldehydes affords mono- and disubstituted hydroxyalkylaminoimidazoles and tetrahydropurine derivatives. The formation of the tetrahydropurine is believed to proceed via an intermolecular hetero [2+4] cycloaddition between 2-aminoimidazole and its corresponding Schiff base.
引用
收藏
页码:6981 / 6984
页数:4
相关论文
共 32 条
[1]   2-AMINOIMIDAZOLES AND THEIR ZINC-COMPLEXES FROM INDO-PACIFIC LEUCETTA SPONGES AND NOTODORIS NUDIBRANCHS [J].
ALVI, KA ;
PETERS, BM ;
HUNTER, LM ;
CREWS, P .
TETRAHEDRON, 1993, 49 (02) :329-336
[2]   PURINE STUDIES .20. METHYLATION AND REDUCTION OF 2,8-DIOXOPURINES, 2,8-DIAMINOPURINES, AND 2-AMINO-8-OXO-PURINES, AND STEREOCHEMISTRY OF THEIR 1,4,5,6-TETRAHYDRO-DERIVATIVES [J].
ARMAREGO, WLF ;
REECE, PA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (13) :1414-1424
[3]   STRUCTURE OF A CRYSTALLINE DERIVATIVE OF SAXITOXIN - STRUCTURE OF SAXITOXIN [J].
BORDNER, J ;
THIESSEN, WE ;
BATES, HA ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (21) :6008-6012
[4]   SYNTHESIS OF PARAZOANTHOXANTHINS AND PSEUDOZOANTHOXANTHINS [J].
BRAUN, M ;
BUCHI, G ;
BUSHEY, DF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (13) :4208-4213
[5]   NEW LEUKOTRIENE-B4 RECEPTOR ANTAGONIST - LEUCETTAMINE-A AND RELATED IMIDAZOLE ALKALOIDS FROM THE MARINE SPONGE LEUCETTA-MICRORAPHIS [J].
CHAN, GW ;
MONG, S ;
HEMLING, ME ;
FREYER, AJ ;
OFFEN, PH ;
DEBROSSE, CW ;
SARAU, HM ;
WESTLEY, JW .
JOURNAL OF NATURAL PRODUCTS, 1993, 56 (01) :116-121
[6]  
CHEVOLOT L, 1981, MARINE NATURAL PRODU, V4, P53
[7]  
CHRISTOPHERSEN C, 1985, ALKALOIDS CHEM PHARM, V24, P25
[8]   OCCURRENCE OF HYDROXYHYDROQUINONE AND 2-AMINOIMIDAZOLE IN SPONGES [J].
CIMINO, G ;
DESTEFAN.S ;
MINALE, L .
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY, 1974, 47 (4B) :895-897
[9]   A DIASTEREOSELECTIVE SYNTHESIS OF GIROLLINE [J].
COMMERCON, A ;
GUEREMY, C .
TETRAHEDRON LETTERS, 1991, 32 (11) :1419-1422
[10]   SYNTHESIS OF 2-DIMETHYLAMINOIMIDAZOLE DERIVATIVES - A NEW ACCESS TO INDOLYL-IMIDAZOLE ALKALOIDS OF MARINE ORIGIN [J].
DALKAFOUKI, A ;
ARDISSON, J ;
KUNESCH, N ;
LACOMBE, L ;
POISSON, JE .
TETRAHEDRON LETTERS, 1991, 32 (39) :5325-5328