Iodine-Mediated Oxidative Cyclization of 2-(Pyridin-2-yl)acetate Derivatives with Alkynes: Condition-Controlled Selective Synthesis of Multisubstituted Indolizines

Synthesis ◽  
2019 ◽  
Vol 52 (03) ◽  
pp. 459-470 ◽  
Author(s):  
Lisheng He ◽  
Yuzhu Yang ◽  
Xiaolan Liu ◽  
Guangyan Liang ◽  
Chunyan Li ◽  
...  
Keyword(s):  
Oxidative Cyclization ◽  
Cyclization Reaction ◽  
Selective Synthesis ◽  
Reaction Conditions ◽  
Stepwise Synthesis

An iodine-mediated oxidative cyclization reaction between 2-(pyridin-2-yl)acetate derivatives and different alkynes has been developed, which provides regioselective and chemoselective syntheses of multiply substituted indolizines under modified reaction conditions. Plausible mechanisms have been proposed to explain the selective syntheses of indolizines. This protocol can be also applied to the stepwise synthesis of 2,2′-biindolizines.

Metal-Free Oxidative C(sp3)–N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 912-917 ◽  
Author(s):  
Parviz Ranjbar ◽  
Narjes Rezaei ◽  
Ehsan Sheikhi
Keyword(s):  
Oxidative Cyclization ◽  
Cyclization Reaction ◽  
Primary Amines ◽  
Isatoic Anhydride ◽  
Reaction Conditions ◽  
Coupling Process ◽  
Benzylic Alcohols ◽  
Metal Free ◽  
Novel Synthesis

A metal-free oxidative C(sp3)–N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1H)-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium bromide to form alkoxysulfonium intermediates. These intermediates undergo an oxidative cyclization reaction with primary amines and isatoic anhydride to produce the title products.

scholarly journals Synthesis and Antitumor Activity of a Series of Novel 1-Oxa-4-azaspiro[4,5]deca-6,9-diene-3,8-dione Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 936
Author(s):  
Ze Yang ◽  
Qiu Zhong ◽  
Shilong Zheng ◽  
Guangdi Wang ◽  
Ling He
Keyword(s):  
Cell Line ◽  
Cell Lines ◽  
Cancer Cell ◽  
Cancer Cell Lines ◽  
Oxidative Cyclization ◽  
Human Lung Cancer ◽  
Reaction Conditions ◽  
Promising Candidate ◽  
Metal Catalyzed ◽  
Further Development

A series of novel 1-oxa-4-azaspiro[4.5]deca-6,9-diene-3,8-diones were designed and synthesized by using 4-aminophenol and α-glycolic acid or lactic acid as starting materials in three or four steps. The key step is the metal-catalyzed oxidative cyclization of the amide to 1-oxa-4-azaspiro[4.5]deca-6,9-diene-3,8-diones (10a and 10b), the reaction conditions of which are investigated and optimized. The anticancer activity of 17 1-oxa-4-azaspiro[4.5]deca-6,9-diene-3,8-dione derivatives was evaluated. Preliminary results showed that 15 compounds have moderate to potent activity against human lung cancer A549, human breast cancer MDA-MB-231, and human cervical cancer HeLa cancer cell lines. Among them, compounds 11b and 11h were the most potent against A549 cell line with 0.18 and 0.19 µM of IC50, respectively; compounds 11d, 11h, and 11k showed the most potent cytotoxicity against MDA-MB-231 cell line with 0.08, 0.08, and 0.09 µM of IC50, respectively, while the activities of 11h, 11k, and 12c against HeLa cell line were the most potent with 0.15, 0.14, and 0.14 µM of IC50, respectively. Compound 11h is a promising candidate for further development, which emerged as the most effective compound overall against the three tested cancer cell lines.

Synthetic and Mechanistic Studies on 2,3-Dihydrobenzo[b][1,4]-oxaselenines Formation from Selenocyanates

Synthesis ◽  
2020 ◽  
Vol 52 (11) ◽  
pp. 1643-1658
Author(s):  
Sergio H. Szajnman ◽  
Juan B. Rodriguez ◽  
María N. Chao ◽  
Mauricio Cattaneo ◽  
Jonathan Sanchez Gonzalez ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Aromatic Ring ◽  
Relevant Information ◽  
Point Of View ◽  
Cyclization Reaction ◽  
Mechanistic Studies ◽  
Reaction Conditions

An expedient preparation of selenium-containing hetero­cycles via an m-chloroperbenzoic acid-mediated seleno-annulation starting from selenocyanate derivatives is described. In spite of its significance, this cyclization reaction is virtually understudied not only from the point of view of its scope, but also from the mechanistic aspects associated to this remarkable transformation. In this sense, several selenocyanate and thiocyanate derivatives bearing an aromatic ring were evaluated as substrates under different reaction conditions of this interesting cyclization yielding important insights on its scope as well as relevant information on the reaction mechanism.

Sequential multicomponent site-selective synthesis of 4-iodo and 5-iodopyrrole-3-carboxaldehydes from a common set of starting materials by tuning the conditions

2020 ◽  
Vol 18 (6) ◽  
pp. 1155-1164 ◽  
Author(s):  
Sachin Choudhary ◽  
Jyothi Yadav ◽  
Mamta ◽  
Amol Prakash Pawar ◽  
Satheeshvarma Vanaparthi ◽  
...  
Keyword(s):  
Selective Synthesis ◽  
Reaction Conditions ◽  
Straightforward Method ◽  
High Yields ◽  
Site Selective

A simple and straightforward method for the synthesis of 4-iodo and 5-iodopyrrole-3-carboxaldehydes is developed in good to high yields (up to 78%) from a common set of starting materials by tuning the reaction conditions.

Copper(II)-Promoted Oxidation/[3+2]Cycloaddition/Aromatization Cascade: Efficient Synthesis of Tetrasubstituted NH-Pyrrole from Chalcones and Iminodiacetates

Synlett ◽  
2019 ◽  
Vol 30 (12) ◽  
pp. 1442-1446 ◽  
Author(s):  
Zhang-qi Lin ◽  
Chao-dong Li ◽  
Zi-chun Zhou ◽  
Shuai Xue ◽  
Jian-rong Gao ◽  
...  
Keyword(s):  
Efficient Method ◽  
Cascade Reaction ◽  
Oxidative Cyclization ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Wide Range ◽  
Reaction Proceeds

A simple and highly efficient method for the preparation of tetrasubstituted NH-pyrrole from a wide range of chalcones and diethyl iminodiacetates via a Cu(OAc)2-promoted oxidation/[3+2]cycloaddition/aromatization cascade reaction has been developed. This reaction proceeds through dehydrogenations, deamination, and oxidative cyclization, affording the corresponding products in good to excellent yields. This convenient methodology for constructing tetrasubstituted NH-pyrroles has several advantages over existing methods, such as the use of easily accessible chalcones and readily available diethyl iminodiacetates, and mild reaction conditions. A wide range of substrates are tolerated.

A Surprising Formation of Novel Bridged Bis-Benzimidazoles by Oxidation of Diaminoquinoxalines

2012 ◽  
Vol 67 (4) ◽  
pp. 367-372 ◽  
Author(s):  
Jens Preßler ◽  
Rainer Beckert ◽  
Sven Rau ◽  
Roberto Menzel ◽  
Eckhard Birckner ◽  
...  
Keyword(s):  
Visible Spectrum ◽  
Oxidative Cyclization ◽  
Cyclization Reaction ◽  
High Melting ◽  
Strong Fluorescence ◽  
Blue Region ◽  
Derivatives Of

A synthesis of novel hexacyclic bis-benzimidazoles 6 starting from 2,3-diarylamino-quinoxalines via an oxidative cyclization cascade is described. These very stable and high-melting derivatives are featured by their strong fluorescence in the blue region of the visible spectrum. The cyclization reaction between 2,3-dichloroquinoxaline and 1,2-phenylenediamine did not lead to derivatives of type 6. In this case, only fluoflavine 7 was isolated quantitatively.

Oxidative Cyclization Reaction of 2-Aryl-Substituted Cinnamates To Form Phenanthrene Carboxylates by Using MoCl5

2014 ◽  
Vol 20 (39) ◽  
pp. 12463-12469 ◽  
Author(s):  
Kathrin Wehming ◽  
Moritz Schubert ◽  
Gregor Schnakenburg ◽  
Siegfried R. Waldvogel
Keyword(s):  
Oxidative Cyclization ◽  
Cyclization Reaction

Oxidative transformation of N-substituted 2-aminophenols to 2-substituted benzoxazoles catalyzed by polymer-incarcerated and carbon-stabilized platinum nanoclusters

2012 ◽  
Vol 90 (3) ◽  
pp. 306-313 ◽  
Author(s):  
Woo-Jin Yoo ◽  
Hao Yuan ◽  
Hiroyuki Miyamura ◽  
Shū Kobayashi
Keyword(s):  
Composite Material ◽  
Carbon Black ◽  
Aerobic Oxidation ◽  
Oxidative Cyclization ◽  
Cyclization Reaction ◽  
Oxidative Transformation ◽  
Platinum Nanoclusters

The preparation of 2-substituted benzoxazoles was achieved through a sequential aerobic oxidation – enolization – oxidative cyclization reaction of N-substituted 2-aminophenols catalyzed by platinum nanoclusters supported on a polymer / carbon black composite material.

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