Efficient Organocatalytic Dual Activation Strategy for Preparing the Versatile Synthons (2E)-1-(Het)Aryl/styryl-3-(dimethylamino)prop-2-en-1-ones and α-(E)-[(Dimethylamino)methylene]cycloalkanones

被引：16
作者：
Bindal, Sachin [1 ]
Kumar, Dinesh [1 ]
Kommi, Damodara N. [1 ]
Bhatiya, Sonam [1 ]
Chakraborti, Asit K. [1 ]
机构：
[1] NIPER, Sas Nagar 160062, Punjab, India
来源：
SYNTHESIS-STUTTGART | 2011年 / 12期
关键词：
2-guanidinoacetic acid; organocatalyst; dual activation; 3-(dimethylamino)propenones; aryl methyl ketone; N; N-dimethylformamide dimethyl acetal; MICROWAVE-ASSISTED SYNTHESIS; IONIC LIQUID CATALYSIS; O-ALKYL CLEAVAGE; HIGHLY EFFICIENT; CONDENSATION; ENAMINONES; PROTOCOL; ESTER; GENERATION; KETONES;
D O I：
10.1055/s-0030-1260048
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel organocatalytic dual activation strategy is reported for an efficient synthesis of the versatile synthons (2E)-1-aryl/heteroaryl/styryl-3-(dimethylamino)prop-2-en-1-ones and alpha-(E)-[(dimethylamino)methylene]cycloalkanones. 2-Guanidinoacetic acid (10 mol%) serves as an ambifunctional organocatalyst for the reaction of various aryl/heteroaryl/styryl methyl ketones and cyclic ketones having an a-methylene moiety with N,N-dimethylformamide dimethyl acetal at 100 degrees C for 1-3 hours under solvent-free conditions to afford the corresponding (2E)-3-(dimethylamino)prop-2-en-1-ones in 72-95% yields.
引用
收藏
页码：1930 / 1935
页数：6
相关论文
共 42 条
[1]   EFFICIENT CONVERSION OF KETONES TO ALPHA-UNSATURATED,BETA-UNSATURATED KETONES [J].
ABDULLA, RF ;
FUHR, KH .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4248-4250
[2]   Microwave assisted synthesis, part 1: Rapid solventless synthesis of 3-substituted coumarins and benzocoumarins by microwave irradiation of the corresponding enaminones [J].
Al-Zaydi, KM .
MOLECULES, 2003, 8 (07) :541-555
[3]   Chemoselective O-methylation of phenols under non-aqueous condition [J].
Basak, A ;
Nayak, MK ;
Chakraborti, AK .
TETRAHEDRON LETTERS, 1998, 39 (27) :4883-4886
[4]   LiOH•H2O as a novel dual activation catalyst for highly efficient and easy synthesis of 1,3-diaryl-2-propenones by Claisen-Schmidt condensation under mild conditions [J].
Bhagat, S ;
Sharma, R ;
Sawant, DM ;
Sharma, L ;
Chakraborti, AK .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 244 (1-2) :20-24
[5]   Dual-activation protocol for tandem cross-aldol condensation:: An easy and highly efficient synthesis of α,α′-bis(aryl/alkylmethylidene)ketones [J].
Bhagat, Srikant ;
Sharma, Ratnesh ;
Chakraborti, Asit K. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 260 (1-2) :235-240
[6]   Reaction of methyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate with ureas:: facile entry into the polycyclic meridianin analogues with uracil structural unit [J].
Casar, Z ;
Bevk, D ;
Svete, J ;
Stanovnik, B .
TETRAHEDRON, 2005, 61 (31) :7508-7519
[7]   Parallel solution-phase synthesis of (Z)-3-(arylamino)-2,3-dehydroalanine derivatives and solid-phase synthesis of fused pyrimidones [J].
Cebasek, P ;
Wagger, J ;
Bevk, D ;
Jakse, R ;
Svete, J ;
Stanovnik, B .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (03) :356-362
[8]   Influence of hydrogen bonding in the activation of nucleophiles:: PhSH-(catalytic) KF in N-methyl-2-pyrrolidone as an efficient protocol for selective cleavage of alkyl/aryl esters and aryl alkyl ethers under nonhydrolytic and neutral conditions [J].
Chakraborti, AK ;
Sharma, L ;
Nayak, MK .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2541-2547
[9]   Demand-based thiolate anion generation under virtually neutral conditions: Influence of steric and electronic factors on chemo- and regioselective cleavage of aryl alkyl ethers [J].
Chakraborti, AK ;
Sharma, L ;
Nayak, MK .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18) :6406-6414
[10]   Selective deprotection of aryl acetates, benzoates, pivalates, and tosylates under nonhydrolytic and virtually neutral conditions [J].
Chakraborti, AK ;
Nayak, MK ;
Sharma, L .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :8027-8030
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