C-NUCLEOSIDES .19. SYNTHESIS OF 7-SUBSTITUTED AND 8-SUBSTITUTED 4-[1-(BETA-D-RIBOFURANOSYL)OXO]-1,3-DIHYDRO-2H-1,5-BENZODIAZEPIN-2-ONE

被引：0
作者：
ITO, Y
WAKIMURA, M
ITO, C
MAEBA, I
机构：
来源：
HETEROCYCLES | 1992年 / 34卷 / 05期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of 7- and 8-substituted 4-[1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)oxo]-1,3-dihydro-2H-1,5-benzodiazepin-2-one from furanone glycoside (1) is described. Treatment of 1,2-diamino-4-substituted benzenes (2a-c) with 1 gave a mixture of 7- and 8-substituted 4-[1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)oxo]-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one (3a-d). Dehydrogenation of 3a-d with DDQ and a trace of PTSA afforded 7- and 8-substituted 4-[1-(2,3,5-tri-O-benzoyl-beta-D-ribo-furanosyl)oxo]-1,3-dihydro-2H-1,5-benzodiazepin-2-ones (4a-f). The position of the substituent in compounds (4a-f) was confirmed by H-1-C-13 long-range COSY and NOE experiments with the corresponding N1-methyl derivatives (5a-c). Deprotection of compounds (4a-e) with methanolic sodium hydroxide afforded 4g-k.
引用
收藏
页码：955 / 964
页数：10
相关论文
共 50 条
[11]   NMR-SPECTRA AND CONFORMATIONAL-ANALYSIS OF SUBSTITUTED 1,3,4,5-TETRAHYDRO-2H-1,5-BENZODIAZEPIN-2-ONE DERIVATIVES [J].
MALIK, F ;
HASSAN, M ;
ROSENBAUM, D ;
DUDDECK, H .
MAGNETIC RESONANCE IN CHEMISTRY, 1989, 27 (04) :391-395
[12]   (4Z)-1-Propargyl(1,3-Dipropargyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one [J].
Said, Ould Mohamed Sidya Mohamed ;
Rachid, Bouhfid ;
Joly, Nicolas ;
Lequart, Vincent ;
Martin, Patrick ;
Massoui, M. ;
Essassi, El Mokhtar .
MOLBANK, 2006, (05)
[13]   SYNTHETIC STUDIES OF POTENTIAL ANTIMETABOLITES .12. SYNTHESIS OF 4-SUBSTITUTED 1-(BETA-D-RIBOFURANOSYL)-1H-IMIDAZO[4,5-C]PYRIDINES [J].
MIZUNO, Y ;
TAZAWA, S ;
KAGEURA, K .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1968, 16 (10) :2011-+
[14]   OLIGONUCLEOTIDE COMPOUNDS .37. SYNTHESIS OF SOME NUCLEOTIDE DERIVATIVES OF 1-(BETA-D-RIBOFURANOSYL)PYRIMID-2-ONE AND 3-(BETA-D-RIBOFURANOSYL)PYRIMID-4-ONE [J].
PISCHEL, H ;
HOLY, A .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1970, 35 (12) :3584-&
[15]   (4Z)-1-Benzyl(1,3-Dibenzyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one [J].
Said, Ould Mohamed Sidya Mohamed ;
Rachid, Bouhfid ;
Joly, Nicolas ;
Lequart, Vincent ;
Martin, Patrick ;
Massoui, M. ;
Essassi, El Mokhtar .
MOLBANK, 2006, (05)
[16]   Synthesis of 5-phenyl-7-chloro-1, 3-dihydro-2H-1, 4-benzodiazepin-2-one under microwave irradiatio [J].
WU, Shuangshuang ;
LU, Yong ;
WANG, Wenfeng ;
HU, Yanfei ;
CHEN, Tianyun .
Huagong Jinzhan/Chemical Industry and Engineering Progress, 2017, 36 (S1) :402-405
[17]   PYRROLOPYRIMIDINE NUCLEOSIDES .I. SYNTHESIS OF 4-SUBSTITUTED 7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINES FROM TUBERCIDIN [J].
GERSTER, JF ;
CARPENTE.B ;
ROBINS, RK ;
TOWNSEND, LB .
JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (03) :326-+
[18]   THE PREPARATION OF 7-CHLORO-5-(2-CHLOROPHENYL)-1, 3-DIHYDRO-2H-1, 4-BENZODIAZEPIN-2-ONE-5-C-14 [J].
KAEGI, HH ;
BURGER, W .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1982, 19 (08) :975-979
[19]   Synthesis of 7H-1,2,4-triazolo[1,5-d](tetrazole acyclo C-nucleosides [J].
Taha, MAM .
HETEROCYCLIC COMMUNICATIONS, 2001, 7 (06) :559-562
[20]   PYRROLOPYRIMIDINE NUCLEOSIDES .19. A TOTAL SYNTHESIS OF THE NUCLEOSIDE ANTIBIOTIC CADEGUOMYCIN [2-AMINO-7-(BETA-D-RIBOFURANOSYL)-PYRROLO[2,3-D]PYRIMIDIN-4-ONE-5-CARBOXYLIC ACID] [J].
BEYLIN, VG ;
KAWASAKI, AM ;
CHENG, CS ;
TOWNSEND, LB .
TETRAHEDRON LETTERS, 1983, 24 (44) :4793-4796
12345