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References (61)
-
Diana Freudendahl, S. Santoro, S. Shahzad, C. Santi, T. Wirth (2009)
Green chemistry with selenium reagents: development of efficient catalytic reactions.Angewandte Chemie, 48 45
-
Diana Freudendahl, Stefano Santoro, Sohail Shahzad, Claudio Santi, T. Wirth (2009)
Grüne Chemie mit Selenreagentien: Entwicklung effizienter katalytischer ReaktionenAngewandte Chemie, 121
-
D. Engel, G. Dudley (2006)
Olefination of ketones using a gold(III)-catalyzed Meyer-Schuster rearrangement.Organic letters, 8 18
-
J. Thanusu, V. Kanagarajan, M. Gopalakrishnan (2010)
Synthesis, spectral characterization, and in vitro antibacterial and antifungal activities of novel 1,3-thiazine-2-amines comprising morpholine nucleusJournal of Enzyme Inhibition and Medicinal Chemistry, 25
-
Janardhana Nayak, K. Girisha, B. Kalluraya, S. Shenoy (2009)
Synthesis, Characterization, and Antimicrobial Studies of Some Quinolines Containing 1,3-ThiazinesPhosphorus, Sulfur, and Silicon and the Related Elements, 184
-
I. Hermecz (1998)
Chemistry of Pyrido[2,1-c][1,4]oxazines, Pyrido[2,1- c][1,4]thiazines, Pyrido[1,2- a]pyrazines and TAdvances in Heterocyclic Chemistry
-
S. Cho, M. Koketsu, H. Ishihara, M. Matsushita, A. Nairn, H. Fukazawa, Y. Uehara (2000)
Novel compounds, '1,3-selenazine derivatives' as specific inhibitors of eukaryotic elongation factor-2 kinase.Biochimica et biophysica acta, 1475 3
-
I. Levshin, A. Tsurkan, É. Rudzit, G. Neshchadim (1981)
Synthesis and antimicrobial activity of selenazolidinone-4 derivativesPharmaceutical Chemistry Journal, 15
-
K. Burger, E. Huber, W. Schöntag, R. Ottlinger (1983)
4H-1,3-oxazines, 4,5-dihydro-oxazoles, and thia analogues from hetero-1,3-dienes and 1-alkynesJournal of The Chemical Society, Chemical Communications
-
H. Kai, Yasuhide Morioka, Minoru Tomida, Tadashi Takahashi, Maki Hattori, K. Hanasaki, Katsumi Koike, Hiroki Chiba, Shun-ichi Shinohara, T. Kanemasa, Y. Iwamoto, Kohji Takahashi, Y. Yamaguchi, T. Baba, T. Yoshikawa, H. Takenaka (2007)
2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 2: orally bioavailable compounds.Bioorganic & medicinal chemistry letters, 17 14
-
(2010)
Facile one-pot synthesis of three different substituted thiazoles from propargylic alcohols -
Beatriz Romano, M. Font, I. Encío, J. Palop, C. Sanmartín (2014)
Synthesis and antiproliferative activity of novel methylselenocarbamates.European journal of medicinal chemistry, 83
-
J. Trenner, Christian Depken, T. Weber, Alexander Breder (2013)
Direct oxidative allylic and vinylic amination of alkenes through selenium catalysis.Angewandte Chemie, 52 34
-
M. Vovk, N. Golovach, V. Sukach (2010)
Optically active 4-aryl-4-trifluoromethyl-4H-1,3-oxa(thia)zinesJournal of Fluorine Chemistry, 131
-
K. Okamoto, Y. Nishibayashi, S. Uemura, A. Toshimitsu (2005)
Asymmetric carboselenenylation reaction of alkenes with aromatic compounds.Angewandte Chemie, 44 23
-
T. Trofimova, O. Zefirova, A. Mandrugin, V. Fedoseev, D. Peregud, M. Onufriev, N. Gulyaeva, S. Proskuryakov (2008)
Synthesis and study of NOS-inhibiting activity of 2-N-acylamino-5,6-dihydro-4H-1,3-thiazineMoscow University Chemistry Bulletin, 63
-
Xiaoxiang Zhang, W. Teo, Sally, P. Chan (2010)
Brønsted acid catalyzed cyclization of propargylic alcohols with thioamides. Facile synthesis of di- and trisubstituted thiazoles.The Journal of organic chemistry, 75 18
-
M. Koketsu, Kohsuke Tanaka, Yuichi Takenaka, C. Kwong, H. Ishihara (2002)
Synthesis of 1,3-thiazine derivatives and their evaluation as potential antimycobacterial agents.European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 15 3
-
L. Fodor, Péter Csomós, A. Csámpai, P. Sohår (2010)
A Convenient Synthesis of 1,4-Benzothiazepinesfrom 1,3-Benzothiazines via the Ring Transformation of β-Lactam-Condensed1,3-Benzothiazine DerivativesSynthesis, 2010
-
F. Fülöp, G. Bernáth, K. Pihlaja (1997)
Synthesis, Stereochemistry and Transformations of Cyclopentane-, Cyclohexane-, Cycloheptane-, and Cyclooctane-Fused 1,3-Oxazines, 1,3-Thiazines, and PyrimidinesAdvances in Heterocyclic Chemistry, 69
-
T. Gilchrist (1996)
6.04 – 1,2-Oxazines and their Benzo Derivatives, 6
-
M. Sainsbury (1996)
6.24 – Six-membered Rings with Two or More Heteroatoms with at least one Selenium or Tellurium, 6
-
A. Proshin, I. Serkov, A. Lermontov, E. Shevtsova, M. Neganova, S. Bachurin (2013)
Novel bicyclic derivatives of 1,3-selenazineRussian Chemical Bulletin, 62
-
K. Nicolaou, N. Winssinger, R. Hughes, C. Smethurst, S. Cho (2000)
New Selenium-Based Safety-Catch Linkers: Solid-Phase Semisynthesis of VancomycinAngewandte Chemie, 39
-
L. Fodor, Péter Csomós, A. Csámpai, P. Sohår, T. Holczbauer, A. Kălmăn (2011)
Expected and unexpected reactions of 1,3-benzothiazine derivatives, II. Formation of isomeric 5,6-dihydro-1,5-benzothiazocinesTetrahedron Letters, 52
-
S. Khokhar, T. Wirth (2004)
Selenocyclisierungen: Kontrolle durch Koordination und GegenionAngewandte Chemie, 116
-
A. Demain, S. Sánchez (2009)
Microbial drug discovery: 80 years of progressThe Journal of Antibiotics, 62
-
J. Trenner, Christian Depken, T. Weber, Alexander Breder (2013)
Direkte oxidative allylische und vinylische Aminierung von Alkenen mittels SelenkatalyseAngewandte Chemie, 125
-
W. Wu, K. Murakami, M. Koketsu, Y. Yamada, I. Saiki (1999)
Induction of apoptosis in human gastric adenocarcinoma cells by two novel organoselenium compounds, TS-2 and TS-6.Anticancer research, 19 6B
-
Yi Fang, Shun‐Yi Wang, Xiaobin Shen, S. Ji (2015)
Base-promoted cascade reaction of isocyanides, selenium and amines: a practical approach to 2-aminobenzo[d][1,3]selenazines under metal-free conditionsOrganic chemistry frontiers, 2
-
R. Schmidt (1972)
1,3-Oxazines and 1,3-Thiazines, Intermediates of Interest in Organic SynthesesSynthesis, 1972
-
Xue-Rong Zhao, M.‐D. Ruan, Wei-Qiang Fan, Xun-Jun Zhou (1994)
Convenient Synthesis of Primary Selenoamides from Aryl Nitriles, Selenium, and Sodium BorohydrideSynthetic Communications, 24
-
L. Fodor, Péter Csomós, T. Holczbauer, A. Kălmăn, A. Csámpai, P. Sohår (2011)
Expected and unexpected reactions of 1,3-benzothiazine derivatives, I. Ring transformation of β-lactam-condensed 1,3-benzothiazines into 4,5-dihydro-1,4-benzothiazepines and indolo-1,4-benzothiazepinesTetrahedron Letters, 52
-
H. Kai, Yasuhide Morioka, Takami Murashi, K. Morita, Satomi Shinonome, H. Nakazato, K. Kawamoto, K. Hanasaki, F. Takahashi, S. Mihara, Tohko Arai, K. Abe, H. Okabe, T. Baba, T. Yoshikawa, H. Takenaka (2007)
2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 1: discovery of CB2 receptor selective compounds.Bioorganic & medicinal chemistry letters, 17 14
-
Flavie Peudru, J. Lohier, M. Gulea, V. Reboul (2016)
Synthesis of 1,3-thiazines by a three-component reaction and their transformations into β-lactam-condensed 1,3-thiazine and 1,4-thiazepine derivativesPhosphorus, Sulfur, and Silicon and the Related Elements, 191
-
S. Shahzad, T. Wirth (2009)
Fast synthesis of benzofluorenes by selenium-mediated carbocyclizations.Angewandte Chemie, 48 14
-
Y. Liu, Badru-Deen Barry, Hai-feng Yu, Jianquan Liu, Peiqiu Liao, X. Bi (2013)
Regiospecific 6-endo-annulation of in situ generated 3,4-dienamides/acids: synthesis of δ-lactams and δ-lactones.Organic letters, 15 11
-
P. Torres-García, E. Viñuelas-Zahínos, F. Luna-Giles, J. Espino, F. Barros-García (2011)
Zinc(II) complexes with novel 1,3-thiazine/pyrazole derivative ligands: Synthesis, structural characterization and effect of coordination on the phagocytic activity of human neutrophilsPolyhedron, 30
-
M. Suárez, H. Novoa, Y. Verdecia, E. Ochoa, A. Alvarez, R. Pérez, R. Martínez‐Álvarez, Dolores Molero, C. Seoane, N. Blaton, O. Peeters, N. Martín (2006)
A straightforward synthesis and structure of unprecedented iminium salts of dihydropyrido[3,2-e][1,3]thiazinesTetrahedron, 62
-
M. Sainsbury (1996)
6.05 – 1,3-Oxazines and their Benzo Derivatives, 6
-
F. Jose, Shilpa Lal, S. Lekshmi, Jiju, E. Abraham (2017)
PURIFIED WATER FROM URINE: A REVIEWJournal of Pharmaceutical and Scientific Innovation, 6
-
H. El‐Sayed, M. El-Hashash, A. Ahmed (2018)
Novel synthesis, ring transformation and anticancer activity of 1,3-thiazine, pyrimidine and triazolo[1,5-a]pyrimidine derivativesBulletin of The Chemical Society of Ethiopia, 32
-
S. Blokhina, T. Volkova, M. Ol’khovich, A. Sharapova, A. Proshin, G. Perlovich (2014)
Solubility and Solution Thermodynamics of Novel Bicyclic Derivatives of 1,3-Selenazine in Biological Relevant SolventsJournal of Chemical & Engineering Data, 59
-
N. Ingarsal, P. Amutha, S. Nagarajan (2006)
Synthesis and antibacterial activities of some 2-amino-4-(1,1′-biphenyl-4-yl)-6-aryl-6H-1,3-thiazinesJournal of Sulfur Chemistry, 27
-
R. Bairam, Srinivasa Muppavarapu, S. Sreekanth (2017)
SYNTHESIS, CHARACTERIZATION, BIOLOGICAL EVALUATION AND DOCKING OF SOME NOVEL SUBSTITUTED 1, 3-THIAZINE DERIVATIVESInternational Journal of Pharmacy and Pharmaceutical Sciences, 9
-
Shaista Khokhar, T. Wirth (2004)
Selenocyclizations: control by coordination and by the counterion.Angewandte Chemie, 43 5
-
M. Koketsu, H. Ishihara, W. Wu, K. Murakami, I. Saiki (1999)
1,3-Selenazine derivatives induce cytotoxicity and DNA fragmentation in human HT-1080 fibrosarcoma cells.European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 9 2
-
M. Koketsu, T. Senda, Katsuhiro Yoshimura, H. Ishihara (1999)
Synthesis and characterization of novel 1,3-selenazine derivatives. BF3·Et2O-assisted reaction of primary selenoamides with α,β-unsaturated ketonesJournal of The Chemical Society-perkin Transactions 1
-
F. Anderson, C. Duca, J. Scudi (1951)
Some Heterocyclic ThiosemicarbazonesJournal of the American Chemical Society, 73
-
A. Al-Rubaie, L. Yousif, A. Al-Hamad (2002)
Palladium-catalyzed formation of 3,5-diaryl-1,2,4-selenadiazoles from arylselenocarboxamideJournal of Organometallic Chemistry, 656
-
H. Quiniou, O. Guilloton (1991)
1,3-ThiazinesChemInform, 22
-
Sohail Shahzad, T. Wirth (2009)
Schnelle Synthese von Benzofluorenen durch selenvermittelte CarbocyclisierungenAngewandte Chemie, 121
-
M. Yoshimatsu, Teruhisa Yamamoto, Arisa Sawa, Tomohiro Kato, G. Tanabe, O. Muraoka (2009)
Alpha-sulfanyl and alpha-selanyl propadienyl cations: regioselective generations and cycloadditions with thioamides and selemides controlled by MeNO2-H2O system.Organic letters, 11 13
-
Riyako Terazawa, Dinesh Garud, Nanako Hamada, Y. Fujita, T. Itoh, Y. Nozawa, K. Nakane, T. Deguchi, M. Koketsu, Masafumi Ito (2010)
Identification of organoselenium compounds that possess chemopreventive properties in human prostate cancer LNCaP cells.Bioorganic & medicinal chemistry, 18 19
-
D. Bózsing, P. Sohår, G. Gigler, G. Kovács (1996)
Synthesis and pharmacological study of new 3,4-dihydro-2H,6H-pyrimido-[2,1-b][1,3]thiazinesEuropean Journal of Medicinal Chemistry, 31
-
B. Draghici, B. El-Gendy, A. Katritzky (2012)
Synthesis of Benzoxazines, Quinazolinesand 4H-Benzo[e][1,3]thiazineby ANRORC Rearrangements of 1,2,4-OxadiazolesSynthesis, 44
-
Li-Na Fu, D. Ye, Ying Li, Shu-fan Yin (2010)
Synthesis and calming activity of 6H-2-Amino-4-Aryl-6-(4-β-D-Allopyranosyloxyphenyl)-1,3-ThiazineChemistry of Natural Compounds, 46
-
B. Tozkoparan, G. Aktay, E. Yeşilada (2002)
Synthesis of some 1,2,4-triazolo[3,2-b]-1,3-thiazine-7-ones with potential analgesic and antiinflammatory activities.Farmaco, 57 2
-
Nagihan Beyhan, B. Koçyiğit-Kaymakçıoğlu, S. Gümrü, F. Aricioglu (2017)
SYNTHESIS AND ANTICONVULSANT ACTIVITY OF SOME 2-PYRAZOLINES DERIVED FROM CHALCONESArabian Journal of Chemistry, 10
-
Xian Huang*, Lei Yu, Zhenhua Chen (2005)
Tandem Michael–Nucleouphilic Addition of 2‐Cyclopropylidene Propionaldehyde—A Novel Method for the Synthesis of Spirocyclopropane‐Annulated HeterocyclesSynthetic Communications, 35
-
Yuanxun Zhu, Guangwei Yin, D. Hong, P. Lu, Yanguang Wang (2011)
Tandem reaction of propargylic alcohol, sulfonamide, and N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide.Organic letters, 13 5
- Publisher
- Wiley
- Copyright
- © 2021 Wiley‐VCH GmbH
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.202000563
- Publisher site
- See Article on Publisher Site
Abstract
An efficient strategy for the synthesis of 3,4‐dihydro‐2H‐1,3‐thiazines / 3,4‐dihydro‐2H‐1,3‐selenazines from propargylic alcohols and thioamides/thiosemicarbazones/selenamides is described. The reaction is accomplished in moderate to excellent yield under mild conditions that did not require the exclusion of air or moisture and offers an operationally simplistic and convenient route to the synthetically useful six‐membered N,S/Se‐heterocycles.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Jan 1, 2021
Keywords: ; ; ; ;