通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Peoples R China.
摘要:
A synergistic I2/amine promoted formal [4 + 2] cycloaddition of methyl ketones, arylamines, and aryl(alkyl)acetaldehydes as alkene surrogates has been established. This protocol allowed the modular synthesis of various 2-acyl-3-aryl(alkyl)quinolines, rather than 2,4-substituted quinolines. Notably, the arylamines not only participated as reactants in this reaction but also acted as indispensable catalysts to promote enamine formation. Moreover, mechanistic investigation suggested that the reaction occurred via an iodination/Kornblum oxidation/Povarov/aromatization sequence.
通讯机构:
[Wu, YD; Wu, AX] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
A highly efficient I2-promoted formal [4 + 2] cycloaddition has been developed for the synthesis of 2-acylquinolines from methyl ketones and arylamines using 1,4-dithane-2,5-diol as an ethylene surrogate. Moreover, the investigation of the mechanism suggested that this reaction occurred via an iodination/Kornblum oxidation/Povarov/aromatization sequence. It is noteworthy that the arylamine substrate also played an important role in promoting the reaction.
通讯机构:
[Wu, YD; Wu, AX] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.
摘要:
An efficient transition-metal-free cascade reaction has been developed for the facile synthesis of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one derivatives from commercially available isatins and 2-haloaryl isothiocyanates. A preliminary mechanistic study suggested an interrupted Dimroth rearrangement was the key step for the successful transformation.
作者机构:
[Wu, An-Xin; Jia, Feng-Cheng; Zhou, Zhi-Wen; Xu, Cheng; Wu, Yan-Dong] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Wu, An-Xin] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构:
[Wu, An-Xin] L;[Wu, YD; Wu, AX] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
摘要:
A synergetic tert-butyl hydroperoxide/K3PO4-promoted oxidative cyclization has been developed for the facile synthesis of various functionalized quinazolin-4(3H)-ones from commercially available isatins and amidine hydrochlorides at room temperature. The synthetic utility of this strategy was illustrated by the convenient synthesis of tryptanthrin derivatives via a self-dimerization of isatins under the same conditions.
通讯机构:
[Wu, YD; Wu, AX] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.
摘要:
An unusual benzannulation reaction has been realized by integrating intermolecular adol condensation with subsequent intramolercular base-promoted homolytic aromatic substitution. This novel cascade reaction provides a straightforward approach toward various naphtho-fused oxindoles from 2-halobenzaldehydes and indolin-2-ones in the presence of Cs2CO3 in DMSO. The enolates of indolin-2-ones as new and internal electron donors have been demonstrated to initiate intramolecular radical dehalogenative coupling.
通讯机构:
[Shu, WM; Wu, AX] C;[Shu, Wen-Ming] Y;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.;Yangtze Univ, Coll Chem & Environm Engn, Jingzhou 434023, Peoples R China.
摘要:
A transition-metal-free coupling annulation reaction of arynes, ketones, and alkynoates has been demonstrated. Using this formal [2 + 2 + 2] cycloaddition reaction, a wide variety of naphthalene derivatives were conveniently constructed in one pot with high efficiency. In addition, this novel and valid annulation has been successfully applied to the synthesis of 1-phenanthrenol derivatives.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
An efficient three-component domino reaction of 2-bromoaldehydes, benzylamines, and sodium azide has been developed for the synthesis of quinazoline derivatives. This domino process involves copper-catalyzed SNAr, oxidation/cyclization, and denitrogenation sequences. The mild catalytic system enabled the effective construction of three C-N bonds in one operation.
摘要:
A base-promoted domino reaction to synthesize the 2,3-disubstituted indoles from 2-aminobenzaldehyde/2-amino aryl ketones, tosylhydrazine, and aromatic aldehydes has been developed. This strategy provides a simple and beneficial way for the construction of 2,3-disubstituted indole compounds from readily available starting materials under mild conditions.
通讯机构:
[Wu, YD; Wu, AX] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
A highly efficient molecular iodine mediated Radziszewski-type reaction of methyl ketones, anilines, and tosylmethyl isocyanide has been developed. This protocol represents an elegant molecular fragment assembly of imidazoles via a formal [2 + 1 + 1 + 1] annulation. It is the first example where methyl ketones serve as the α-dicarbonyl compounds and aldehydes in Radziszewski-type reactions.
通讯机构:
[Wu, YD; Wu, AX] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
摘要:
A highly para-selective C-C bond coupling is presented between phenols C(sp(2)) and aryl methyl ketones C(sp(3)), which enables the direct construction of 4-hydroxybenzil derivatives. This practical method exhibits a broad substrate scope and large-scale applicability and represents a general gateway to the hydroxybenzil natural product family. Mechanistic investigations indicated that the combination of HI with DMSO realized the oxidative carbonylation of aryl methyl ketones, while boric acid acted as a dual-functional relay reagent to promote this transformation.
通讯机构:
[Wu, YD; Wu, AX] C;Cent China Normal Univ, Minist Educ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
An acid-catalyzed multicomponent tandem double cyclization protocol has been developed for the synthesis of polyfunctional 4,9-dihydropyrrolo[2,1-b]quinazolines from simple and readily available arylglyoxal monohydrates, 2-aminobenzylamine, and trans-β-nitrostyrenes. This practical and metal-free reaction proceeds through an imine formation/cyclization/Michael addition/Henry cyclization protocol, resulting in the construction of four new bonds and two ring moieties directly in one pot.
通讯机构:
[Wu, YD; Wu, AX] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.
摘要:
An acid-catalyzed multicomponent tandem cyclization protocol has been developed for the synthesis of polyfunctional dihydroindolizino[8,7-b]indoles from simple and readily available arylglyoxal monohydrates, tryptamines, and trans-beta-nitrostyrenes or malononitrile. This reaction represents a highly efficient and convenient methodology for the synthesis of diversely substituted heteropolycyclic scaffolds under mild, metal-free conditions.
通讯机构:
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
摘要:
An unprecedented direct dual C-H bond functionalization of unprotected anilines and methyl ketones has been demonstrated. It is the first example of iodine-promoted highly chemo- and site-selective oxidative C-H/C-H cross-coupling of anilines and methyl ketones to furnish the C4-dicarbonylation of anilines in moderate to good yields. Moreover, coproduct HI acted as a catalyst in the reaction. The salient feature of this approach is unprecedented C-H functionalization rather than N-H functionalization of unprotected anilines.