Auto-redox reaction:: Tin(II) chloride-mediated one-step reductive cyclization leading to the synthesis of novel biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity

被引:71
作者
Roy, AD [1 ]
Subramanian, A [1 ]
Roy, R [1 ]
机构
[1] Cent Drug Res Inst, Div SAIF, Lucknow 226001, Uttar Pradesh, India
关键词
D O I
10.1021/jo0518912
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A tin(II) chloride-mediated short, efficient, and practical regioselective synthesis of biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity is reported. A one-step reductive transformation of 2-(2-nitrophenyl)-3H-quinazolin-4-one in various alcohols furnished the desired tetracyclic product in good yields with high purity.
引用
收藏
页码:382 / 385
页数:4
相关论文
共 41 条
  • [1] Novel approaches for the solid-phase synthesis of biheterocyclic dihydroimidazole analogues
    Acharya, AN
    Ostresh, JM
    Houghten, RA
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (03): : 214 - 222
  • [2] PALLADIUM COMPLEX-CATALYZED INTERMOLECULAR REDUCTIVE N-HETEROCYCLIZATION - NOVEL SYNTHESIS OF QUINAZOLINE DERIVATIVES FROM 2-NITROBENZALDEHYDE OR 2-NITROPHENYL KETONES WITH FORMAMIDE
    AKAZOME, M
    YAMAMOTO, J
    KONDO, T
    WATANABE, Y
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 494 (1-2) : 229 - 233
  • [3] Novel series of 8H-quinazolino[4,3-b]quinazolin-8-ones via two Niementowski condensations
    Alexandre, FR
    Berecibar, A
    Wrigglesworth, R
    Besson, T
    [J]. TETRAHEDRON, 2003, 59 (09) : 1413 - 1419
  • [4] [Anonymous], 2003, HDB HETEROCYCLIC CHE
  • [5] Arya P, 2001, ANGEW CHEM INT EDIT, V40, P339, DOI 10.1002/1521-3773(20010119)40:2<339::AID-ANIE339>3.0.CO
  • [6] 2-J
  • [7] BERENTSVEIG VV, 1979, REACT KINET CATAL L, V10, P333
  • [8] 1-AMINOACYL-2,3-DIHYDRO-4(1H)-QUINAZOLINONE DERIVATIVES WITH CHOLERETIC AND ANTIFIBRILLATORY ACTIVITY
    BONOLA, G
    DARE, P
    MAGISTRE.MJ
    MASSARAN.E
    SETNIKAR, I
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (06) : 1136 - &
  • [9] A facile S-transalkylation of 2,2′-bipyridine alkyl sulfides -: a new tool for the synthesis of annulated biheterocycles
    Branowska, D
    Rykowski, A
    Wysocki, W
    [J]. TETRAHEDRON LETTERS, 2005, 46 (37) : 6223 - 6226
  • [10] Synthesis of 1,3-diamino-7,8,9,10-tetrahydropyrido[3,2-f]-quinazolines. Inhibitors of Candida albicans dihydrofolate reductase as potential antifungal agents
    Chan, JH
    Hong, JS
    Kuyper, LF
    Jones, ML
    Baccanari, DP
    Tansik, RL
    Boytos, CM
    Rudolph, SK
    Brown, AD
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (01) : 145 - 151