FeCl3‑Promoted Carboxamidation and Cyclization of Aryl Isonitriles with Formamides toward Phenanthridine-6-carboxamides
An iron-promoted tandem carboxamidation and cyclization between aryl isonitriles and formamides has been developed. The one-pot strategy can be applied to a wide range of 2-isocyanobiphenyls and formamides with excellent functional group tolerance for the synthesis of phenanthridine-6-carboxamides i...
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| Published in | Journal of organic chemistry Vol. 79; no. 20; pp. 9907 - 9912 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
17.10.2014
Amer Chemical Soc |
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| Abstract | An iron-promoted tandem carboxamidation and cyclization between aryl isonitriles and formamides has been developed. The one-pot strategy can be applied to a wide range of 2-isocyanobiphenyls and formamides with excellent functional group tolerance for the synthesis of phenanthridine-6-carboxamides in moderate to excellent yields. |
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| AbstractList | An iron-promoted tandem carboxamidation and cyclization between aryl isonitriles and formamides has been developed. The one-pot strategy can be applied to a wide range of 2-isocyanobiphenyls and formamides with excellent functional group tolerance for the synthesis of phenanthridine-6-carboxamides in moderate to excellent yields. |
| Author | Zhang, Xing-Guo Chu, Jing-Jing Liu, Yu-Rong Hu, Bo-Lun Tu, Hai-Yong |
| AuthorAffiliation | College of Chemistry and Materials Engineering Wenzhou University |
| AuthorAffiliation_xml | – name: Wenzhou University – name: College of Chemistry and Materials Engineering |
| Author_xml | – sequence: 1 givenname: Hai-Yong surname: Tu fullname: Tu, Hai-Yong – sequence: 2 givenname: Yu-Rong surname: Liu fullname: Liu, Yu-Rong – sequence: 3 givenname: Jing-Jing surname: Chu fullname: Chu, Jing-Jing – sequence: 4 givenname: Bo-Lun surname: Hu fullname: Hu, Bo-Lun – sequence: 5 givenname: Xing-Guo surname: Zhang fullname: Zhang, Xing-Guo email: zxg@wzu.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25244055$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/jm8005433 10.1021/jo4007255 10.1002/anie.201108763 10.1021/jo201542x 10.1021/jm300021v 10.1021/ja203495c 10.1021/ol101490n 10.1021/ol500277u 10.1021/ol4022589 10.1021/ol5018195 10.1134/S0030400X06030131 10.1039/c0cs00196a 10.1039/c2cc30351e 10.1021/jp046016j 10.1016/j.bmc.2005.07.033 10.1039/c4ob01256a 10.1021/ja8008924 10.1039/b808625g 10.1021/jo3027033 10.1038/nature10702 10.1016/j.tet.2005.08.031 10.1002/anie.200804683 10.1021/ol403256e 10.1039/c1cc13086b 10.1002/anie.201306082 10.1021/np030529k 10.1021/jo2017108 10.1021/ol501461u 10.1055/s-0028-1083277 10.1039/c3cc49026b 10.1021/jm300943r 10.1002/anie.200902400 10.1002/anie.201206115 10.1021/ol403147v 10.1021/ja204226n 10.1002/chem.201200888 10.1021/ol4026827 10.1039/c4cc03304c 10.1038/nrd1133 10.1007/s11426-014-5118-7 10.1016/j.tetlet.2005.12.134 10.1039/c2gc35880h 10.1002/anie.201308376 |
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| Keywords | 2-ISOCYANOBIPHENYLS PHENANTHRIDINE DERIVATIVES ETHER C BOND FORMATION AMIDATION OXIDATIVE CYCLIZATION INHIBITORS H ACTIVATION AMIDES 6-(TRIFLUOROMETHYL)PHENANTHRIDINES |
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| References | Read, ML (WOS:000314558300058) 2013; 78 Nakanishi, T (WOS:000081140100013) 1999; 62 Goossen, LJ (WOS:000262526200021) 2009 Dubost, E (WOS:000311461500024) 2012; 55 Peng, JL (WOS:000301673200026) 2012; 48 Ghosh, S (WOS:000310156300037) 2012; 14 Nakanishi, T (WOS:000089955800020) 2000; 10 FANG, SD (WOS:A1993LY88900001) 1993; 58 Bray, BL (WOS:000183713400020) 2003; 2 Li, ZJ (WOS:000337869800057) 2014; 16 Li, KL (WOS:000302591100039) 2012; 55 Zhang, J (WOS:000228982900027) 2005; 109 Liu, ZJ (WOS:000301792000031) 2012; 51 Sha, WX (WOS:000339930400038) 2014; 50 Humphrey, JM (WOS:A1997XZ27000010) 1997; 97 Zhang, B (WOS:000329472800065) 2014; 16 He, T (WOS:000293086400064) 2011; 47 Intrieri, D (WOS:000307387300003) 2012; 18 Candito, DA (WOS:000269361300032) 2009; 48 Nakanishi, T (WOS:000076681800017) 1998; 61 Hesp, KD (WOS:000293872800009) 2011; 133 HUDSON, D (WOS:A1988M076300026) 1988; 53 Jiang, H (WOS:000327802100027) 2013; 52 Denny, WA (WOS:000177652100002) 2002; 9 Gerfaud, T (WOS:000262539800023) 2009; 48 Nandita, G. (000343527200056.34) 2004 Liu, J (WOS:000330775500019) 2014; 50 Leifert, D (WOS:000329077700045) 2013; 15 Ishikawa, T (WOS:000166067800002) 2001; 21 Cheng, YZ (WOS:000326615100032) 2013; 15 Zhang, B (WOS:000339982300036) 2014; 16 Tobisu, M (WOS:000310874400035) 2012; 51 Liu, WP (WOS:000293113200021) 2011; 133 Portela-Cubillo, F (WOS:000259306700025) 2008 Wang, L (WOS:000334823600004) 2014; 16 Peng, JS (WOS:000296754400035) 2011; 76 Zhang, LN (WOS:000280799100030) 2010; 12 Linsenmeier, AM (WOS:000296206400057) 2011; 76 Lee, MJ (WOS:000235647300034) 2006; 47 Wang, WY (WOS:000320979500022) 2013; 78 Zhu, SJ (WOS:000233391800023) 2005; 13 Pan, CD (WOS:000340084700019) 2014; 57 Abdel-Halim, OB (WOS:000222901000009) 2004; 67 Stevens, N (WOS:000256550600008) 2008; 130 Allen, CL (WOS:000291807600002) 2011; 40 Zhang, B (WOS:000325157600024) 2013; 52 Montalbetti, CAGN (WOS:000232908100001) 2005; 61 Wang, QL (WOS:000330159700056) 2013; 15 Zhu, ZQ (WOS:000339470200008) 2014; 12 Nakanishi, T (WOS:000085171900007) 1999; 1 Bondarev, SL (WOS:000239728700013) 2006; 100 Pattabiraman, VR (WOS:000298318000051) 2011; 480 Bernardo, PH (WOS:000260730900013) 2008; 51 |
| References_xml | – volume: 51 start-page: 6699 year: 2008 ident: WOS:000260730900013 article-title: Structure-Activity Relationship Studies of Phenanthridine-Based Bcl-X-L Inhibitors publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm8005433 contributor: fullname: Bernardo, PH – volume: 78 start-page: 6025 year: 2013 ident: WOS:000320979500022 article-title: Synthesis of 6-(Trifluoromethyl)phenanthridines via Palladium-Catalyzed Tandem Suzuki/C-H Arylation Reactions publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo4007255 contributor: fullname: Wang, WY – volume: 51 start-page: 3231 year: 2012 ident: WOS:000301792000031 article-title: Cross Coupling of Acyl and Aminyl Radicals: Direct Synthesis of Amides Catalyzed by Bu4NI with TBHP as an Oxidant publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201108763 contributor: fullname: Liu, ZJ – volume: 76 start-page: 9127 year: 2011 ident: WOS:000296206400057 article-title: Synthesis of Phenanthridine Derivatives via Photolysis publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo201542x contributor: fullname: Linsenmeier, AM – volume: 55 start-page: 3319 year: 2012 ident: WOS:000302591100039 article-title: Optimization of Potent Hepatitis C Virus NS3 Helicase Inhibitors Isolated from the Yellow Dyes Thioflavine S and Primuline publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm300021v contributor: fullname: Li, KL – volume: 133 start-page: 11430 year: 2011 ident: WOS:000293872800009 article-title: Expedient Synthesis of N-Acyl Anthranilamides and beta-Enamine Amides by the Rh(III)-Catalyzed Amidation of Aryl and Vinyl C-H Bonds with Isocyanates publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja203495c contributor: fullname: Hesp, KD – volume: 62 start-page: 864 year: 1999 ident: WOS:000081140100013 article-title: Structural considerations of NK109, an antitumor benzo[c]phenanthridine alkaloid publication-title: JOURNAL OF NATURAL PRODUCTS contributor: fullname: Nakanishi, T – volume: 21 start-page: 61 year: 2001 ident: WOS:000166067800002 article-title: Benzo[c]phenanthridine bases and their antituberculosis activity publication-title: MEDICINAL RESEARCH REVIEWS contributor: fullname: Ishikawa, T – volume: 12 start-page: 3682 year: 2010 ident: WOS:000280799100030 article-title: Copper-Catalyzed Synthesis of Phenanthridine Derivatives under an Oxygen Atmosphere Starting from Biaryl-2-carbonitriles and Grignard Reagents publication-title: ORGANIC LETTERS doi: 10.1021/ol101490n contributor: fullname: Zhang, LN – volume: 16 start-page: 2088 year: 2014 ident: WOS:000334823600004 article-title: The Benzoyl Peroxide Promoted Dual C-C Bond Formation via Dual C-H Bond Cleavage: alpha-Phenanthridinylation of Ether by Isocyanide publication-title: ORGANIC LETTERS doi: 10.1021/ol500277u contributor: fullname: Wang, L – volume: 61 start-page: 1263 year: 1998 ident: WOS:000076681800017 article-title: Revision of the structure of fagaridine based on the comparison of UV and NMR data of synthetic compounds publication-title: JOURNAL OF NATURAL PRODUCTS contributor: fullname: Nakanishi, T – volume: 15 start-page: 4846 year: 2013 ident: WOS:000330159700056 article-title: PhI(OAc)(2)-Mediated Synthesis of 6-(Trifluoromethyl)phenanthridines by Oxidative Cyclization of 2-Isocyanobiphenyls with CF3SiMe3 under Metal-Free Conditions publication-title: ORGANIC LETTERS doi: 10.1021/ol4022589 contributor: fullname: Wang, QL – volume: 16 start-page: 3990 year: 2014 ident: WOS:000339982300036 article-title: 6-Perfluoroalkylated Phenanthridines via Radical Perfluoroalkylation of Isonitriles publication-title: ORGANIC LETTERS doi: 10.1021/ol5018195 contributor: fullname: Zhang, B – volume: 100 start-page: 386 year: 2006 ident: WOS:000239728700013 article-title: Picosecond dynamics of singlet excited states of oxotetrahydrobenzo[c]phenanthridine in protic and aprotic solvents publication-title: OPTICS AND SPECTROSCOPY doi: 10.1134/S0030400X06030131 contributor: fullname: Bondarev, SL – volume: 40 start-page: 3405 year: 2011 ident: WOS:000291807600002 article-title: Metal-catalysed approaches to amide bond formation publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c0cs00196a contributor: fullname: Allen, CL – volume: 48 start-page: 3772 year: 2012 ident: WOS:000301673200026 article-title: Direct carboxamidation of indoles by palladium-catalyzed C-H activation and isocyanide insertion publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c2cc30351e contributor: fullname: Peng, JL – volume: 109 start-page: 8701 year: 2005 ident: WOS:000228982900027 article-title: Enhanced luminescence of phenyl-phenanthridine dye on aggregated small silver nanoparticles publication-title: JOURNAL OF PHYSICAL CHEMISTRY B doi: 10.1021/jp046016j contributor: fullname: Zhang, J – volume: 13 start-page: 6782 year: 2005 ident: WOS:000233391800023 article-title: Esters and amides of 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine-12-carboxylic acid: Potent cytotoxic and topoisomerase I-targeting agents publication-title: BIOORGANIC & MEDICINAL CHEMISTRY doi: 10.1016/j.bmc.2005.07.033 contributor: fullname: Zhu, SJ – volume: 97 start-page: 2243 year: 1997 ident: WOS:A1997XZ27000010 article-title: Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides publication-title: CHEMICAL REVIEWS contributor: fullname: Humphrey, JM – volume: 12 start-page: 5839 year: 2014 ident: WOS:000339470200008 article-title: A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines via dual C(sp(3))-H/C(sp(2))-H functionalizations publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c4ob01256a contributor: fullname: Zhu, ZQ – start-page: 574 year: 2004 ident: 000343527200056.34 publication-title: Synlett contributor: fullname: Nandita, G. – volume: 130 start-page: 7182 year: 2008 ident: WOS:000256550600008 article-title: Two color RNA intercalating probe for cell imaging applications publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja8008924 contributor: fullname: Stevens, N – volume: 58 start-page: 5025 year: 1993 ident: WOS:A1993LY88900001 article-title: INHIBITORS OF DNA TOPOISOMERASE-I ISOLATED FROM THE ROOTS OF ZANTHOXYLUM-NITIDUM publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: FANG, SD – start-page: 4189 year: 2008 ident: WOS:000259306700025 article-title: From dioxime oxalates to dihydropyrroles and phenanthridines via iminyl radicals publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b808625g contributor: fullname: Portela-Cubillo, F – volume: 78 start-page: 1311 year: 2013 ident: WOS:000314558300058 article-title: Synthesis of Phenanthridine Derivatives by Microwave-Mediated Cyclization of o-Furyl(allylamino)arenes publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo3027033 contributor: fullname: Read, ML – volume: 480 start-page: 471 year: 2011 ident: WOS:000298318000051 article-title: Rethinking amide bond synthesis publication-title: NATURE doi: 10.1038/nature10702 contributor: fullname: Pattabiraman, VR – volume: 9 start-page: 1655 year: 2002 ident: WOS:000177652100002 article-title: Acridine derivatives as chemotherapeutic agents publication-title: CURRENT MEDICINAL CHEMISTRY contributor: fullname: Denny, WA – volume: 61 start-page: 10827 year: 2005 ident: WOS:000232908100001 article-title: Amide bond formation and peptide coupling publication-title: TETRAHEDRON doi: 10.1016/j.tet.2005.08.031 contributor: fullname: Montalbetti, CAGN – volume: 48 start-page: 572 year: 2009 ident: WOS:000262539800023 article-title: Palladium-Catalyzed Annulation of Acyloximes with Arynes (or Alkynes) Synthesis of Phenanthridines and Isoquinolines publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200804683 contributor: fullname: Gerfaud, T – volume: 16 start-page: 250 year: 2014 ident: WOS:000329472800065 article-title: 6-Phosphorylated Phenanthridines from 2-Isocyanobiphenyls via Radical C-P and C-C Bond Formation publication-title: ORGANIC LETTERS doi: 10.1021/ol403256e contributor: fullname: Zhang, B – volume: 47 start-page: 8946 year: 2011 ident: WOS:000293086400064 article-title: Direct amidation of azoles with formamides via metal-free C-H activation in the presence of tert-butyl perbenzoate publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c1cc13086b contributor: fullname: He, T – volume: 1 start-page: 985 year: 1999 ident: WOS:000085171900007 article-title: Synthesis and cytotoxic activities of a new benzo[c]phenanthridine alkaloid, 7-hydroxynitidine, and some 9-oxygenated benzo[c]phenanthridine derivatives publication-title: ORGANIC LETTERS contributor: fullname: Nakanishi, T – volume: 52 start-page: 10792 year: 2013 ident: WOS:000325157600024 article-title: 6-Trifluoromethyl-Phenanthridines through Radical Trifluoromethylation of Isonitriles publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201306082 contributor: fullname: Zhang, B – volume: 53 start-page: 617 year: 1988 ident: WOS:A1988M076300026 article-title: METHODOLOGICAL IMPLICATIONS OF SIMULTANEOUS SOLID-PHASE PEPTIDE-SYNTHESIS .1. COMPARISON OF DIFFERENT COUPLING PROCEDURES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: HUDSON, D – volume: 67 start-page: 1119 year: 2004 ident: WOS:000222901000009 article-title: New crinine-type alkaloids with inhibitory effect on induction of inducible nitric oxide synthase from Crinum yemense publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np030529k contributor: fullname: Abdel-Halim, OB – volume: 76 start-page: 9507 year: 2011 ident: WOS:000296754400035 article-title: Palladium-Catalyzed intramolecular C-H Activation/C-C Bond Formation: A Straightforward Synthesis of Phenanthridines publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo2017108 contributor: fullname: Peng, JS – volume: 16 start-page: 3396 year: 2014 ident: WOS:000337869800057 article-title: A Free Radical Cascade Cyclization of Isocyanides with Simple Alkanes and Alcohols publication-title: ORGANIC LETTERS doi: 10.1021/ol501461u contributor: fullname: Li, ZJ – start-page: 160 year: 2009 ident: WOS:000262526200021 article-title: The Thermal Amidation of Carboxylic Acids Revisited publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0028-1083277 contributor: fullname: Goossen, LJ – volume: 50 start-page: 2145 year: 2014 ident: WOS:000330775500019 article-title: Synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation-cyclization of alpha-oxocarboxylates and isocyanides publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c3cc49026b contributor: fullname: Liu, J – volume: 55 start-page: 9693 year: 2012 ident: WOS:000311461500024 article-title: Synthesis and Structure-Affinity Relationships of Selective High-Affinity 5-HT4 Receptor Antagonists: Application to the Design of New Potential Single Photon Emission Computed Tomography Tracers publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm300943r contributor: fullname: Dubost, E – volume: 48 start-page: 6713 year: 2009 ident: WOS:000269361300032 article-title: Palladium-Catalyzed Domino Direct Arylation/N-Arylation: Convenient Synthesis of Phenanthridines publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200902400 contributor: fullname: Candito, DA – volume: 51 start-page: 11363 year: 2012 ident: WOS:000310874400035 article-title: Modular Synthesis of Phenanthridine Derivatives by Oxidative Cyclization of 2-Isocyanobiphenyls with Organoboron Reagents publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201206115 contributor: fullname: Tobisu, M – volume: 15 start-page: 6286 year: 2013 ident: WOS:000329077700045 article-title: 6-Aroylated Phenanthridines via Base Promoted Homolytic Aromatic Substitution (BHAS) publication-title: ORGANIC LETTERS doi: 10.1021/ol403147v contributor: fullname: Leifert, D – volume: 133 start-page: 10756 year: 2011 ident: WOS:000293113200021 article-title: Iron-Catalyzed Carbonylation-Peroxidation of Alkenes with Aldehydes and Hydroperoxides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja204226n contributor: fullname: Liu, WP – volume: 18 start-page: 10487 year: 2012 ident: WOS:000307387300003 article-title: [Ru(TPP)CO]-Catalysed Intramolecular Benzylic C?H Bond Amination, Affording Phenanthridine and Dihydrophenanthridine Derivatives publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201200888 contributor: fullname: Intrieri, D – volume: 15 start-page: 5520 year: 2013 ident: WOS:000326615100032 article-title: Isocyanide Insertion: De Novo Synthesis of Trifluoromethylated Phenanthridine Derivatives publication-title: ORGANIC LETTERS doi: 10.1021/ol4026827 contributor: fullname: Cheng, YZ – volume: 50 start-page: 9179 year: 2014 ident: WOS:000339930400038 article-title: The benzoyl peroxide-promoted functionalization of simple alkanes with 2-aryl phenyl isonitrile publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c4cc03304c contributor: fullname: Sha, WX – volume: 10 start-page: 2321 year: 2000 ident: WOS:000089955800020 article-title: Synthesis of derivatives of NK109, 7-OH benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction-resistant properties publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS contributor: fullname: Nakanishi, T – volume: 2 start-page: 587 year: 2003 ident: WOS:000183713400020 article-title: Large-scale manufacture of peptide therapeutics by chemical synthesis publication-title: NATURE REVIEWS DRUG DISCOVERY doi: 10.1038/nrd1133 contributor: fullname: Bray, BL – volume: 57 start-page: 1172 year: 2014 ident: WOS:000340084700019 article-title: Tandem dual C(sp(3))-H/C(sp(2))-H functionalization: a radical cyclization of 2-isocyanobiphenyl with ether to 6-alkylated phenanthridine publication-title: SCIENCE CHINA-CHEMISTRY doi: 10.1007/s11426-014-5118-7 contributor: fullname: Pan, CD – volume: 47 start-page: 1833 year: 2006 ident: WOS:000235647300034 article-title: Base-catalyzed domino reaction toward 3-benzylidenecyclohexenes: DBU-promoted sequential Michael, aldol, dehydration, and dealkoxycarbonylation publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2005.12.134 contributor: fullname: Lee, MJ – volume: 14 start-page: 3220 year: 2012 ident: WOS:000310156300037 article-title: Direct amide bond formation from carboxylic acids and amines using activated alumina balls as a new, convenient, clean, reusable and low cost heterogeneous catalyst publication-title: GREEN CHEMISTRY doi: 10.1039/c2gc35880h contributor: fullname: Ghosh, S – volume: 52 start-page: 13289 year: 2013 ident: WOS:000327802100027 article-title: Synthesis of 6-Alkylated Phenanthridine Derivatives Using Photoredox Neutral Somophilic Isocyanide Insertion publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201308376 contributor: fullname: Jiang, H |
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| Snippet | An iron-promoted tandem carboxamidation and cyclization between aryl isonitriles and formamides has been developed. The one-pot strategy can be applied to a... |
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| SubjectTerms | Catalysis Chemistry Chemistry, Organic Chlorides - chemistry Cyclization Ferric Compounds - chemistry Formamides - chemistry Molecular Structure Nitriles - chemistry Phenanthridines - chemical synthesis Phenanthridines - chemistry Physical Sciences Science & Technology Stereoisomerism |
| Title | FeCl3‑Promoted Carboxamidation and Cyclization of Aryl Isonitriles with Formamides toward Phenanthridine-6-carboxamides |
| URI | http://dx.doi.org/10.1021/jo502022c http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000343527200056 https://www.ncbi.nlm.nih.gov/pubmed/25244055 https://search.proquest.com/docview/1613946846 |
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