2532-74-3Relevant academic research and scientific papers
Direct synthesis of dihydrobenzo[a]carbazoles via palladium-catalyzed domino annulation of indoles
Jafarpour, Farnaz,Hazrati, Hamideh
, p. 363 - 367 (2010)
A straightforward one-step synthesis of annulated indoles via palladium-catalyzed, norbornene-mediated sequential intermolecular aryl ortho-alkylation/intramolecular indole C-H activation has been devised. This method provides an efficient route to a wide variety of substituted 6,11-dihydro-5H-benzo[a]carbazoles from readily accessible 3-bromoalkylindoles and iodoarenes.
Cascade dearomatization of N-substituted tryptophols via Lewis acid-catalyzed Michael reactions
Liu, Chuan,Zhang, Wei,Dai, Li-Xin,You, Shu-Li
, p. 7177 - 7183 (2012)
Lewis acid-catalyzed cascade dearomatization of N-substituted tryptophols via Michael addition reaction was developed. The generality of the method has been demonstrated by the synthesis of versatile furoindoline derivatives with a quaternary carbon center in good yields.
AMINOPEPTIDASE A INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
-
, (2020/06/10)
The present invention relates to a novel compound, to a composition comprising the same, to methods for preparing the compound, and the use of this compound in therapy. In particular, the present invention relates to compound that is useful in the treatment and prevention of primary and secondary arterial hypertension, ictus, myocardial ischaemia, cardiac and renal insufficiency, myocardial infarction, peripheral vascular disease, diabetic proteinuria, Syndrome X and glaucoma.
Exploration of a KI-catalyzed oxidation system for direct construction of bispyrrolidino[2,3-: B] indolines and the total synthesis of (+)-WIN 64821
Chen, Si-Kai,Yang, Ju-Song,Dai, Kun-Long,Zhang, Fu-Min,Zhang, Xiao-Ming,Tu, Yong-Qiang
supporting information, p. 121 - 124 (2019/12/30)
A facile and environmentally benign KI(cat.)/NaBO3·4H2O oxidation system has been developed for the tandem oxidative aminocyclization/coupling of tryptamines, affording a series of 3a,3a′-bispyrrolidino[2,3-b]indolines with high efficiency (up to 94% yield). This reaction features an electrophilic "I+" mechanism, which is importantly quite different from and milder than the typical radical-involving process, and can be readily amplified for the total synthesis of (+)-WIN 64821.
Rapid One-Pot Access to Unique 3,4-Dihydrothiopyrano[3,4-b]indol-1(9H)-imines via Bi(OTf)3-Catalysed Tandem Friedel–Crafts Alkylation/Thia-Michael Addition
Dethe, Dattatraya H.,Boda, Vijay Kumar,Mandal, Anupam
supporting information, p. 5417 - 5421 (2018/10/20)
A highly efficient and atom economical one-pot annulation strategy for novel tetrahydrothiopyrano[3,4-b]indoles is presented. This protocol involves a Bi(OTf)3 catalyzed tandem Friedel–Crafts alkylation and intramolecular thia-Michael addition reactions to furnish target molecules in an efficient manner. The method works effectively on substrates with unprotected indoles and also it is successfully employed to make tetrahydrothiepino[3,4-b]indoles. The scaffolds synthesized are diverse and first of the kind. The reaction is practically simple with broad substrate scope and vast functional group compatibility.
Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation
Gu, Yanlong,Huang, Wenbo,Chen, Shaomin,Wang, Xin
supporting information, p. 4285 - 4289 (2018/07/29)
A three-component reaction of indoles, α-bromoacetaldehyde acetals, and ketones was developed by using bismuth(III) triflate as the catalyst to realize a straightforward approach for synthesizing carbazole derivatives. The reaction was established mechanistically through the autotandem catalysis of Bi(OTf)3 in the following two steps: (i) Friedel-Crafts-type alkylation of indole with α-bromoacetaldehyde acetal, which produced a tryptaldehyde-type intermediate and (ii) [4 + 2] annulation of this intermediate with the ketone component.
Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds
Fu, Liangbing,Davies, Huw M. L.
, p. 1504 - 1507 (2017/04/13)
An efficient synthesis of tetrahydrocarboline-type products and polycyclic spiroindolines has been achieved. The transformation proceeds via rhodium(II)-catalyzed intramolecular annulations of indolyl- and pyrrolyl-tethered N-sulfonyl-1,2,3-triazoles. The reaction could be tuned toward either the formal [3 + 2] cycloaddition or the C-H functionalization reaction depending on the electronic and structural features of the substrates, leading to the production of a variety of structurally related heterocyclic compounds.
Four-component, five-centered, one-pot synthesis of 1-(1H-tetrazol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole derivatives
Reddy, B.V. Subba,Kota, Kavya,Rao, B. Maheshwar,Sridhar,Mukkanti
supporting information, p. 4529 - 4532 (2016/09/23)
An efficient four component, five centered coupling strategy has been developed for the synthesis of a novel series of 1-tetrazolyl-tetrahydro-β-carboline derivatives in good yields. This method is effective for the synthesis of tetrazolyl tetrahydro-β-carbolines in a one-pot operation. This method is operationally simple and works under mild conditions with diverse substrates.
Dearomative Indole (3 + 2) Reactions with Azaoxyallyl Cations - New Method for the Synthesis of Pyrroloindolines
DiPoto, Maria C.,Hughes, Russell P.,Wu, Jimmy
supporting information, p. 14861 - 14864 (2015/12/08)
Herein, we report the first examples of the synthesis of pyrroloindolines by means of (3 + 2) dearomative annulation reactions between 3-substituted indoles and highly reactive azaoxyallyl cations. Computational studies using density functional theory (DFT) (B3LYP-D3/6-311G++) support a stepwise reaction pathway in which initial C-C bond formation takes place at C3 of indole, followed by ring closure to give the observed products. Insights gleaned from these calculations indicate that the solvent, either TFE or HFIP, can stabilize the transition state through H-bonding interactions with oxygen of the azaoxyallyl cation and other relevant intermediates, thereby increasing the rates of these reactions.
A short and highly convergent approach for the synthesis of rutaecarpine derivatives
Subba Reddy,Anji Babu,Jagan Mohan Reddy,Sridhar,Ramalinga Murthy,Pranathi,Kalivendi, Shasi V.,Prabhakar Rao
, p. 27476 - 27480 (2015/03/30)
A novel and highly convergent approach has been developed for the synthesis of quinazolinocarboline alkaloid, rutaecarpine, analogues by the condensation of anthranilamide with chloroaldehyde derived from tryptophol. This method also provides direct access to benzimidazocarbolines and quinazolinoisoquinolines. It is a shorter and metal-free approach which does not require any catalyst or additive to facilitate the reaction.
