Stereoselective syntheses of chiral (3S,9bS)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones

被引：18

作者：

Katritzky, AR ^{[1
]}

He, HY ^{[1
]}

Verma, AK ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(02)00220-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral (3S,9bS)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones 11a-11f, 14b.14c and 17a,b were prepared in 78-93% yields with high stereoselectivities (d.e. >99%) by the intermolecular condensations of 2-formylbenzoic acids 10 or 13 or 2-acetylbenzoic acid 15 with chiral diamines 9a-9f and 9h. Compounds 9a-9f and 9h were readily prepared in three steps from optically active N-Boc-alpha-amino acids 5a-5d. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：933 / 938

页数：6

共 50 条

[41] Synthesis of 2-aryl-2,3-dihydro-4H-[1,2]-thiazino[3,2-a]benzimidazol-4-ones and 7-aryl-2,3,6,7-tetrahydro-5H-imidazo[2,1-b]-1,3-5-ones
Britsun, VN
Lozynskii, MO
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2003, (07): : 1103 - 1108
[42] SIMPLIFIED ANALOGS OF LYSERGIC-ACID .5. DERIVATIVES OF N,N-DIETHYL-1-METHYL-9H-INDENO-1,2,3,9A-TETRAHYDRO[2,1-B]PYRIDINE-3-CARBOXAMIDE
CRAIG, JC
DINNER, A
MULLIGAN, PJ
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12): : 1669 - 1676
[43] Synthesis of 1H-pyrazolo [4′3′:5,6] pyrimido [2,1-A]-isoindol-4(10H)-ones.: Derivatives of a new ring system
Davoodnia, A
Bakavoli, M
Vahedinia, A
Rahimizadeh, M
Roshani, M
HETEROCYCLES, 2006, 68 (04) : 801 - 806
[44] Synthesis of 3-aroylmethylene-1,6,7,11b-tetrahydro-2H-pyrazino-[2,1-a] isoquinolin-4-ones
Gein V.L.
Kasimova N.N.
Varkentin L.I.
Stashina G.A.
Chemistry of Heterocyclic Compounds, 2005, 41 (8) : 1041 - 1044
[45] SYNTHESIS OF 12H-BENZIMIDAZO[2,1-B][1,3]BENZOTHIAZIN-12-ONES, 11H-PYRIDO[3',2'-4,5]IMIDAZO[2,1-B][1,3]BENZOTHIAZIN-11-ONE AND 11H-PYRIDO[3,2-E]PYRIDO[3',2'-4,5]IMIDAZO[2,1-B][1,3]THIAZIN-11-ONE
NAGESWAR, YVD
MURTY, MSR
RAMALINGAM, T
SATTUR, PB
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1988, 27 (12): : 1142 - 1143
[46] Highly Enantioselective Synthesis of 2,3-Dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-ones via Catalytic Asymmetric Intramolecular Cascade Imidization-Nucleophilic Addition-Lactamization
He, Yuwei
Cheng, Chuyu
Chen, Bin
Duan, Kun
Zhuang, Yue
Yuan, Bo
Zhang, Meisan
Zhou, Yougui
Zhou, Zihong
Su, Yu-Jun
Cao, Rihui
Qiu, Liqin
ORGANIC LETTERS, 2014, 16 (24) : 6366 - 6369
[47] Synthesis of 3-aroylmethylene-1,6,7,11b-tetrahydro-2H-pyrazino[2,1-a]isoquinolin-4-ones
Gein, VL
Kasimova, NN
Varkenteen, LI
Stashina, GA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2005, (08): : 1218 - 1221
[48] Discovery of (R)-9-ethyl-1,3,4,10b-tetrahydro-7-trifluoromethylpyrazino[2,1-a]isoindol-6(2H)-one, a selective, orally active agonist of the 5-HT2C receptor
Wacker, Dean A.
Varnes, Jeffrey G.
Malmstrom, Sarah E.
Cao, Xueying
Hung, Chen-Pin
Ung, Thao
Wu, Ginger
Zhang, Ge
Zuvich, Eva
Thomas, Michael A.
Keim, William J.
Cullen, Mary Jane
Rohrbach, Kenneth W.
Qu, Qinling
Narayanan, Rangaraj
Rossi, Karen
Janovitz, Evan
Lehman-McKeeman, Lois
Malley, Mary F.
Devenny, James
Pelleymounter, Mary Ann
Miller, Keith J.
Robl, Jeffrey A.
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (06) : 1365 - 1379
[49] PHARMACOLOGICAL ANALYSIS OF A NEW ANOREXIC SUBSTANCE - 5-HYDROXY-5-(4'-CHLOROPHENYL)-2, 3-DIHYDRO-5H-IMIDAZO-(2,1-A) ISOINDOLE (MAZINDOL
GOGERTY, JH
PENBERTHY, C
IORIO, LC
TRAPOLD, JH
ARCHIVES INTERNATIONALES DE PHARMACODYNAMIE ET DE THERAPIE, 1975, 214 (02): : 285 - 307
[50] STUDIES ON INDENOPYRIDINE DERIVATIVES AND RELATED-COMPOUNDS .5. A FACILE SYNTHESIS OF ETHYL 9,9-DIMETHYL-1,2,3,9A-TETRAHYDRO-9H-INDENO[2,1-B]PYRIDINE-3-CARBOXYLATE
YONEDA, R
TERADA, T
SATODA, S
KURIHARA, T
HETEROCYCLES, 1985, 23 (09) : 2243 - 2246

← 1 2 3 4 5 →