Catalyst-free aldol condensation of ketones and isatins under mild reaction conditions in DMF with molecular sieves 4 Å as additive

被引：47

作者：

Chen, Wen-Bing ^{[1
,2
]}

Liao, Yu-Hua ^{[1
,2
]}

Du, Xi-Lin ^{[3
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

[3] Fourth Mil Med Univ, TangDu Hosp, Dept Gen Surg, Xian 710038, Peoples R China

来源：

GREEN CHEMISTRY | 2009年 / 11卷 / 09期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; PROTEASOME INHIBITORS; CARBONYL-COMPOUNDS; OXINDOLES; FLUORINATION; TMC-95A; ACIDS; METHODOLOGY; CYCLIZATION; EFFICIENT;

D O I：

10.1039/b906684e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of molecular sieve (MS) 4 angstrom in DMF, a catalyst-free aldol condensation of a variety of aromatic and aliphatic ketones with isatins under mild reaction conditions has been developed. This approach may provide access to a wide range of 3-substituted-3-hydroxyindolin-2-ones in good to excellent yields.

引用

页码：1465 / 1476

页数：12

共 60 条

[1] A concise formal total synthesis of TMC-95A/B proteasome inhibitors
Albrecht, BK
Williams, RM
[J]. ORGANIC LETTERS, 2003, 5 (02) : 197 - 200
[2] Metal-mediated entry to functionalized 3-substituted 3-hydroxyindolin-2-ones via regiocontrolled carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions of isatins in aqueous media
Alcaide, B
Almendros, P
Rodríguez-Acebes, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) : 3198 - 3204
[3] Origins, current status, and future challenges of green chemistry
Anastas, PT
Kirchhoff, MM
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) : 686 - 694
[4] Highly diastereoselective arylation of (S)-mandelic acid enolate:: Enantioselective synthesis of substituted (R)-3-hydroxy-3-phenyloxindoles and (R)-benzylic acids and synthesis of nitrobenzophenones
Barroso, S
Blay, G
Cardona, L
Fernández, I
García, B
Pedro, JR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) : 6821 - 6829
[5] 1-Benzopyran-4(4H)-ones as novel activated alkenes in the Baylis-Hillman reaction:: a simple and facile synthesis of indolizine-fused-chromones
Basavaiah, D
Rao, AJ
[J]. TETRAHEDRON LETTERS, 2003, 44 (23) : 4365 - 4368
[6] SYNTHESIS OF THE CARBAZOLE ALKALOIDS HYELLAZOLE AND 6-CHLOROHYELLAZOLE AND RELATED DERIVATIVES
BECCALLI, EM
MARCHESINI, A
PILATI, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (05): : 579 - 587
[7] Condensations of isatm with acetone by the Knoevenagel method
Braude, F
Lindwall, HG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 : 325 - 327
[8] Brown R. K., 1972, INDOLES 1
[9] L-proline-catalyzed asymmetric aldol condensation of N-substituted isatins with acetone
Chen, Gang
Wang, Ye
He, Hongping
Gao, Suo
Yang, Xiaosheng
Hao, Xiaojiang
[J]. HETEROCYCLES, 2006, 68 (11) : 2327 - 2333
[10] Organocatalytic asymmetric aldol reaction of ketones with isatins: straightforward stereoselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones
Chen, Jia-Rong
Liu, Xiao-Peng
Zhu, Xiao-Yu
Li, Liang
Qiao, Yong-Feng
Zhang, Jian-Ming
Xiao, Wen-Jing
[J]. TETRAHEDRON, 2007, 63 (42) : 10437 - 10444

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