180922-71-8Relevant articles and documents
Organocatalytic enantioselective tandem sulfa-Michael/aldol reaction to access dihydrothiopyran-fused benzosulfolane skeletons bearing three contiguous stereocenters
Yang, Lei,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Yuan, Wei-Cheng
, p. 12363 - 12366 (2020)
The first organocatalytic diastereo- and enantioselective tandem sulfa-Michael/aldol reaction of 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes with benzo[b]thiophene sulfones was developed. With multiple hydrogen-bonding thiourea as a catalyst, a wide range of polycyclic dihydrothiopyran-fused benzosulfolanes were smoothly obtained with excellent results (up to 99% yield, 420 : 1 dr and 99% ee) under mild reaction conditions.
A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes
Yang, Lei,Zhou, Shun,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Zhou, Ming-Qiang,Yuan, Wei-Cheng
supporting information, p. 3678 - 3686 (2021/05/05)
The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.
Method for simply and efficiently synthesizing caulerpin
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Paragraph 0043; 0045, (2018/07/30)
The invention belongs to the field of organic chemical synthesis and discloses a method for simply and efficiently synthesizing caulerpin. The method comprises the following steps: by taking 2-indolone as a raw material, firstly, performing halogenated acylation on the 2-indolone, protecting amino on indole, performing nucleophilic substitution at a site 2 of the amino, connecting malonic acid dimethyl, further performing decarboxylation and protection group removal so as to obtain 3-formyl-2-indole methyl acetate, and finally performing cyclization between two molecules, so as to obtain caulerpin. Compared with a disclosed method for synthesizing caulerpin, the method disclosed by the invention is simple in synthesis process, low in raw material cost, gentle in reaction condition, high inproduct purity, high in yield and easy in industrialization, and has a very high medical value and a wide market prospect.
Synthesis of an azabicyclic framework towards (±)-actinophyllic acid
Mortimer, Danny,Whiting, Matthew,Harrity, Joseph P.A.,Jones, Simon,Coldham, Iain
, p. 1255 - 1257 (2014/02/14)
Lewis acid mediated intramolecular Mannich reaction between an azocinone and a 3-formylindole was investigated as part of a study towards the synthesis of actinophyllic acid. The intramolecular Mannich reaction resulted in a single diastereomer of the 1-azabicyclo[4.2.1]nonan-5-one core framework, although single crystal X-ray structure analysis revealed that this had the undesired stereochemistry in comparison with the natural product.
The tertiary amino effect: An efficient method for the synthesis of α-Carbolines
Majumder, Swarup,Bhuyan, Pulak J.
experimental part, p. 173 - 176 (2011/03/22)
Functionalized annelated α-Carbolines have been synthesized from oxindole following a tertiary amino effect reaction strategy. Georg Thieme Verlag Stuttgart New York.
An efficient one-pot, three-component reaction: Synthesis of complex-annelated α-carbolines via an intramolecular [3+2]-dipolar cycloaddition reaction
Majumder, Swarup,Bhuyan, Pulak J.
experimental part, p. 1547 - 1550 (2011/08/04)
Novel annelated α-carbolines have been synthesized from oxindole using three components in a one-pot procedure involving an intramolecular [3+2]-dipolar cycloaddition reaction of azides to nitriles. Georg Thieme Verlag Stuttgart ? New York.
Control of competing N-H insertion and Wolff rearrangement in dirhodium(II)-catalyzed reactions of 3-indolyl diazoketoesters. Synthesis of a potential precursor to the marine 5-(3-indolyl)oxazole martefragin A
Davies, James R.,Kane, Peter D.,Moody, Christopher J.,Slawin, Alexandra M. Z.
, p. 5840 - 5851 (2007/10/03)
Dirhodium(II)-catalyzed reaction of 3-indolyl α-diazo-β- ketoester 25 in the presence of hexanamide results in competing metal carbene N-H insertion and Wolff rearrangement. The corresponding phenyl diazoketoester 32, on the other hand, gives only the product of N-H insertion, suggesting that the indole moiety is more prone to 1,2-rearrangement. The competing processes were investigated in a range of 3-indolyl α-diazo-β-ketoesters (36, 38, 40, 44); these studies established that the Wolff rearrangement could be effectively suppressed by the presence of a strong electron-withdrawing group on the indole nitrogen. Dirhodium(II) catalysts were also more effective than copper or Lewis acid catalysts in favoring the insertion process. The products of N-H insertion, the ketoamides (26, 47, 49, 51, 53), were readily cyclodehydrated to the corresponding 5-(3-indolyl)-oxazoles. The N-H insertion/cyclodehydration methodology was used in a formal synthesis of the marine natural product martefragin A. Thus the N-Boc homoisoleucine amide 23, prepared by asymmetric hydrogenation of a dehydro amino acid, underwent N-H insertion with the rhodium carbene derived from the N-nosyl indolyl diazoester 40, followed by cyclodehydration and deprotection to give the 5-(3-indolyl)oxazole martefragin A precursor 75.
A new approach to the synthesis of rare thiazino[6,5-b]indol-4-one derivatives. First total synthesis of the indole phytoalexin cyclobrassinon
Kutschy, Peter,Suchy, Mojmír,Andreani, Aldo,Dzurilla, Milan,Ková?ik, Vladimír,Alf?ldi, Juraj,Rossi, Maddalena,Gramatová, Mária
, p. 9029 - 9039 (2007/10/03)
The first synthesis of the indole phytoalexin cyclobrassinon and some of its analogues, possessing a thiazino[6,5-b]indol-4-one tricyclic ring system was performed starting from 1-substitued 2-chloroindole-3-carboxaldehydes. The route employed the intramolecular Et3N-mediated or photochemical nucleophilic substitution of a chlorine atom in the 2-position of the indole ring with a sulfur atom as a key step. Examination of biological activity against the selected tumor cell lines, bacteria and fungi revealed no expressive activity of synthesized compounds.
1,3-Thiazino[6,5-b]indol-4-one derivatives. The first synthesis of indole phytoalexin cyclobrassinon
Suchy, Mojmír,Kutschy, Peter,Dzurilla, Milan,Ková?ik, Vladimír,Andreani, Aldo,Alf?ldi, Juraj
, p. 6961 - 6963 (2007/10/03)
The first synthesis of indole phytoalexin cyclobrassinon in six steps, in 12% overall yield and some of its analogues, possessing a 1,3-thiazino[6,5-b]indol-4-one tricyclic ring system was performed, starting from 2-chloroindole-3-carboxaldehyde and employing the intramolecular Et3N-mediated nucleophilic substitution of a chlorine atom in the 2-position of an indole ring with sulfur as a key step.
