Ravi Varala, Mohan Kurra, Mohammed Amanullah, Mohamed Hussien, Mohammed Mujahid Alam
{"title":"Recent methods in the synthesis of chromeno[2,3-d]pyrimidines","authors":"Ravi Varala, Mohan Kurra, Mohammed Amanullah, Mohamed Hussien, Mohammed Mujahid Alam","doi":"10.1007/s10593-024-03302-6","DOIUrl":"https://doi.org/10.1007/s10593-024-03302-6","url":null,"abstract":"<p>The most recent synthetic methods to produce chromeno[2,3-<i>d</i>]pyrimidine derivatives from 2015 onwards are outlined, and this mini-review is divided into different chapters according to the type of the reaction.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141255661","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dmitry V. Osipov, Pavel E. Krasnikov, Alina A. Artemenko
{"title":"A reaction of 2-carbonyl-substituted 1H-benzo[f]chromenes with N-arylamides of cyanoacetic acid","authors":"Dmitry V. Osipov, Pavel E. Krasnikov, Alina A. Artemenko","doi":"10.1007/s10593-024-03312-4","DOIUrl":"https://doi.org/10.1007/s10593-024-03312-4","url":null,"abstract":"<p>A reaction of 2-trifluoroacetyl-1<i>H</i>-benzo[<i>f</i>]chromenes with <i>N</i>-arylamides of cyanoacetic acid led to the synthesis of a series of 2-oxo-6-trifluoromethylpyridine-3-carboxamides as products of a cascade of the carbo-Michael reaction, Thorpe–Ziegler cyclization, and Dimroth rearrangement. In the case of 1<i>H</i>-benzo[<i>f</i>]chromene-2-carbaldehydes, the corresponding Knoevenagel adducts were isolated.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141255441","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Anush Kh. Khachatryan, Katya A. Avagyan, Anush A. Sargsyan, Anait G. Simonyan, Henrik A. Panosyan, Armen G. Ayvazyan, Alik E. Badasyan
{"title":"The synthesis of ethyl 2-amino-1-(aryl)-5-(arylcarbamoyl)-6-oxo-1,6-dihydropyridine-3-carboxylates","authors":"Anush Kh. Khachatryan, Katya A. Avagyan, Anush A. Sargsyan, Anait G. Simonyan, Henrik A. Panosyan, Armen G. Ayvazyan, Alik E. Badasyan","doi":"10.1007/s10593-024-03311-5","DOIUrl":"https://doi.org/10.1007/s10593-024-03311-5","url":null,"abstract":"<p>A new method for the synthesis of previously unknown ethyl 2-amino-1-(aryl)-5-(arylcarbamoyl)-6-oxo-1,6-dihydropyridine-3-carboxylates by a reaction of ethyl 2-cyano-3-ethoxyacrylate with <i>N</i><sup>1</sup>,<i>N</i><sup>3</sup>-diarylmalonamides was developed. The antibacterial activity of some of the synthesized compounds was assayed.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141255655","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Svetlana K. Vorontsova, Alexander M. Scherbakov, Mikhail E. Minyaev, Leonid G. Menchikov, Igor V. Zavarzin
{"title":"The synthesis of furazano- and thiadiazolopyrazine steroids and their antiproliferative activity","authors":"Svetlana K. Vorontsova, Alexander M. Scherbakov, Mikhail E. Minyaev, Leonid G. Menchikov, Igor V. Zavarzin","doi":"10.1007/s10593-024-03319-x","DOIUrl":"https://doi.org/10.1007/s10593-024-03319-x","url":null,"abstract":"<p>An effective method for the synthesis of heterocyclic steroids with the [1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazine and [1,2,5]thiadiazolo[3,4-<i>b</i>]-pyrazine fragments was developed. The structure of the products was confirmed by X-ray structural analysis. The resulting compounds showed high antiproliferative activity against breast (MCF7) and prostate (22Rv1) cancer cells, which was not inferior to that of cisplatin and abiraterone acetate.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141255431","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Alexandra S. Tikhomolova, Zhanna V. Mamleeva, Alevtina Yu. Egorova
{"title":"An efficient synthesis of (E)-3-[(dimethylamino)methylidene]furan-2(3H)-thiones and transamination reactions thereof","authors":"Alexandra S. Tikhomolova, Zhanna V. Mamleeva, Alevtina Yu. Egorova","doi":"10.1007/s10593-024-03309-z","DOIUrl":"https://doi.org/10.1007/s10593-024-03309-z","url":null,"abstract":"<p>The conditions were developed and the optimal temperature regime was selected for a selective thionation of 5-aryl-3-[(dimethylamino)-methylidene]furan-2(3<i>H</i>)-ones with Lawesson's reagent. The stereochemistry of the synthesized 3-[(dimethylamino)methylidene]furan-2(3<i>H</i>)-thiones was established. Based on this, a number of 3-arylaminomethylidenefuran-2(3<i>H</i>)-thiones were synthesized <i>via</i> transamination reaction.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141255384","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of 1,2-oxazine N-oxides via noncatalyzed hetero-Diels–Alder reactions of nitroalkenes (microreview)","authors":"Radomir Jasiński","doi":"10.1007/s10593-024-03304-4","DOIUrl":"https://doi.org/10.1007/s10593-024-03304-4","url":null,"abstract":"\u0000<figure></figure><p>In this microreview, the application of noncatalyzed hetero-Diels–Alder reaction (formally [4+2] cycloaddition) with participation of conjugated nitroalkenes and their analogs for easy and selective preparation of 1,2-oxazine <i>N</i>-oxides was reviewed on the basis of recent publications. It was found that the best described processes are realized with full regioselectivity as well as at mild temperatures. It is interesting, that in some cases of the title reactions, the stepwise mechanism of the formation of the six-membered heterocyclic ring is more possible than classic one-step mechanism.</p><figure><picture><source srcset=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03304-4/MediaObjects/10593_2024_3304_Figd_HTML.png?as=webp\" type=\"image/webp\"/><img alt=\"\" height=\"2\" loading=\"lazy\" src=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03304-4/MediaObjects/10593_2024_3304_Figd_HTML.png\" width=\"685\"/></picture></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141255524","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis and reactivity of [1, 2, 5]thiadiazolo[3,4-b]pyridines and [1, 2, 5]selenadiazolo[3,4-b]pyridines (microreview)","authors":"Maxim A. Bastrakov, Victoria V. Ivanova","doi":"10.1007/s10593-024-03290-7","DOIUrl":"https://doi.org/10.1007/s10593-024-03290-7","url":null,"abstract":"<p>\u0000<img alt=\"\" src=\"//media.springernature.com/lw234/springer-static/image/art%3A10.1007%2Fs10593-024-03290-7/MediaObjects/10593_2024_3290_Figc_HTML.png\" style=\"width:234px;max-width:none;\"/>\u0000The microreview covers the latest selected examples (2013–2024) on the synthesis and reactivity of [1, 2, 5]-thiadiazolo[3,4-<i>b</i>]pyridines and [1, 2, 5]selenadiazolo[3,4-<i>b</i>]pyridines. Their application is also discussed.</p><figure></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-04-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140566563","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ainur D. Sharapov, Ramil F. Fatykhov, Igor A. Khalymbadzha
{"title":"Synthesis of fluorophores based on benzo[g]coumarin framework (microreview)","authors":"Ainur D. Sharapov, Ramil F. Fatykhov, Igor A. Khalymbadzha","doi":"10.1007/s10593-024-03286-3","DOIUrl":"https://doi.org/10.1007/s10593-024-03286-3","url":null,"abstract":"\u0000<figure></figure><p>This microreview summarizes and analyzes literature for the years 2016–2023 on the construction of fluorophores based on benzo[<i>g</i>]coumarin backbone, which represent a push–pull system consisting of an annulated benzo and pyran rings. The main approaches to the synthesis of benzo[<i>g</i>]coumarins are condensation reactions, cyclization reactions, and pyran ring opening reactions followed by recyclization.</p><figure><picture><source srcset=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03286-3/MediaObjects/10593_2024_3286_Figd_HTML.png?as=webp\" type=\"image/webp\"/><img alt=\"\" height=\"2\" loading=\"lazy\" src=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03286-3/MediaObjects/10593_2024_3286_Figd_HTML.png\" width=\"685\"/></picture></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140566557","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of carbonyl-containing nitrofurans (microreview)","authors":"Kirill A. Gomonov, Vasilii V. Pelipko","doi":"10.1007/s10593-024-03285-4","DOIUrl":"https://doi.org/10.1007/s10593-024-03285-4","url":null,"abstract":"\u0000<figure></figure><p>This microreview analyzes and summarizes the most recent advances in the synthesis of carbonyl-containing nitrofurans, including methods of nitration, oxidation, and esterification of the corresponding furan derivatives, published since 2017.</p><figure><picture><source srcset=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03285-4/MediaObjects/10593_2024_3285_Figd_HTML.png?as=webp\" type=\"image/webp\"/><img alt=\"\" height=\"2\" loading=\"lazy\" src=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03285-4/MediaObjects/10593_2024_3285_Figd_HTML.png\" width=\"685\"/></picture></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140566911","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of pyrrolizidine derivatives (microreview)","authors":"Andrey V. Smolobochkin, Tanzilya S. Rizbayeva","doi":"10.1007/s10593-024-03287-2","DOIUrl":"https://doi.org/10.1007/s10593-024-03287-2","url":null,"abstract":"\u0000<figure></figure><p>The review summarizes the methods of synthesis of pyrrolizidine (hexahydro-1<i>H</i>-pyrrolizine) derivatives published in the literature over the past five years. The methods can be conditionally divided into two major groups: synthesis from pyrrolidine derivatives and cyclization of acyclic precursors.</p><figure><picture><source srcset=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03287-2/MediaObjects/10593_2024_3287_Figd_HTML.png?as=webp\" type=\"image/webp\"/><img alt=\"\" height=\"2\" loading=\"lazy\" src=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03287-2/MediaObjects/10593_2024_3287_Figd_HTML.png\" width=\"685\"/></picture></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140566470","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}