Clean synthesis of novel spiro[indene-2, 2'-[1, 3, 5]-oxathiazine]-1, 3-diones in water
- Corresponding author: Azizian Javad, azizian@srbiau.ac.ir
Citation:
Salehpour Mahboobeh, Azizian Javad, Kefayati Hassan. Clean synthesis of novel spiro[indene-2, 2'-[1, 3, 5]-oxathiazine]-1, 3-diones in water[J]. Chinese Chemical Letters,
;2017, 28(5): 1079-1082.
doi:
10.1016/j.cclet.2016.12.036
(a) J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, Germany, 2006;
(b) A. Dömling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106(2006) 17-89;
(c) P. Lu, Y. Wang, Strategies for heterocyclic synthesis via cascade reactions based on ketenimines, Synlett (2010) 165-173;
(d) B. Ganem, Strategies for innovation in multicomponent reaction design, Acc. Chem. Res. 42(2009) 463-472;
(e) D. J. Ramón, M. Yus, Asymmetric multicomponent reactions (AMCRs), Angew. Chem. Int. Ed. 44(2005) 1602-1634.
(a) R. Fringuelli, L. Milanese, F. Schiaffella, Role of 1, 4-benzothiazine derivatives in medicinal chemistry, Mini Rev. Med. Chem. 5(2005) 1061-1073;
(b) H. Li, G. J. Dryhurst, Irreversible inhibition of mitochondrial complex I by 7-(2-aminoethyl)-3, 4-dihydro-5-hydroxy-2H-1, 4-benzothiazine-3-carboxylic acid (DHBT-1): a putative nigral endotoxin of relevance to parkinson's disease, Neurochemistry 69(1997) 153'-1541.
C. Giordano, M. Ferraris, E. Barsuglia. , Methods of combatting nematodes using certain derivatives of 1, 3, 5-oxathiazine, Montedison Fibre SPA, U. S. Patent 4, 035, 496(1977).
(a) W. G. Brouwer, A. R. Bell, A. R. Blem, R. A. Davis, 3-Aryl-5, 6-dihydro-1, 4, 2-oxathiazines and their oxides, U. S. Patent 4, 569, 690, issued February 11(1986).
(b) W. G. Brouwer, A. R. Bell, A. R. Blem, R. A. Davis, 3-Aryl-5, 6-dihydro-1, 4, 2-oxathiazines and their oxides, U. S. Patent 4, 675, 044, issued June 23(1987).
(c) W. G. Brouwer, A. R. Bell, A. R. Blem, R. A. Davis, 3-Aryl-5, 6-dihydro-1, 4, 2-oxathiazines and their oxides, Eur. Patent 0, 104, 940 A1(1984).
(a) J. F. E. Van Gestel, Antibacterial and antifouling oxathiazines and their oxides, U. S. Patent 5, 712, 275, issued January 27(1998).
(b) J. F. E. Van Gestel, Antibacterial and antifouling oxathiazines and their oxides, U. S. Patent 5, 922, 113, issued July 13(1999).
(a) R. A. Davis, A. R. A Valcke, W. G. Brouwer, Uniroyal Chemical Company, Inc. and Uniroyal Chemical Ltd. /Ltee, Wood preservative oxathiazines, U. S. Patent 5, 777, 110(1998).
(b) R. A. Davis, A. R. A Valcke, W. G. Brouwer, Oxathiazine holzschutzmittel, Eur. Patent Speci. 0, 715, 625 B1(1997).
(c) R. A. Davis, A. R. A. Valcke, W. G. Brouwer, Wood preservative oxathiazines, U. S. Patent 6, 372, 297 B1(2002).
(d) L. A. De Witte, A. R. A Valcke, M. A. Van der Flaas, W. M. Willems, Synergistic compositions comprising an oxathiazine and a benzothiophene-2-carboxamide-S, S-dioxide, U. S. Patent 6, 242, 440 B1(2001).
(a) M. Van der Flaas, Preservative formulations comprising an oxathiazine and alkoxylated amines, Eur. Pat. Appl. 1273233 A1(2003). ;
(b) G. L. Chee, B. Bhattarai, R. D. Gietz, et al. , Chemical reactivity and microbicidal action of bethoxazin, Bioorg. Med. Chem. 20(2012) 1494-1501;
(c) S. Hoff, E. Zwanenbug, 6-acetamido-56-dihydro-1, 4, 2-oxathiazines: a novel class of compounds, Tetrahedron Lett. 13(1972) 5267-5268
C. H. Heathcock, S. L. Graham, M. C. Pirrung, F. Plavac, C. T. White, Spirocyclic Systems in the Total Synthesis of Natural Products, vol. Ⅱ, John Wiley & Sons, New York, 1983, pp. p264.
G.S. Singh, Z.Y. Desta. Isatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks[J]. Chem. Rev., 2012,112:6104-6155. doi: 10.1021/cr300135y
(a) A. Alizadeh, R. Ghanbaripour, M. Feizabadi, L. G. Zhu, M. Dusek, Synthesis of 3-[(coumarinyl)carbonyl]-3a, 8b-dihyroindeno[1, 2-b]pyrrole-4(1 H)-ones and their conversion to coumarin bearing spiro[isobenzofuran-1, 2'-pyrrole] moiety compounds via oxidative cleavage reaction, RSC Adv. 5(2015) 80518-80525;
(b) H. Liu, J. Li, M. Xiong, J. Jiang, J. Wang, Cp* coⅢ-catalyzed C-H alkenylation/annulation to afford spiro indenyl benzosultam, J. Org. Chem. 81(2016) 6093-6099;
(c) Z. Yuan, X. Fang, X. Li, et al. , 1, 6-Conjugated addition-mediated[2+1] annulation: approach to spiro[2. 5] octa-47-dien-6-one, J. Org. Chem. 80(2015) 11123-11130.
(a) H. Peng, J. Li, F. Wang, B. Liu, B. Yin, Synthesis of spiro-lactams and polysubstituted pyrroles via ceric ammonium nitrate-mediated oxidative cyclization of N-furan-2-ylmethyl-beta enaminones, J. Org. Chem. 81(2016) 4939-4946;
(c) J. Zheng, W. J. Cui, C. Zheng, S. L. You, Synthesis and application of chiral spiro Cp ligands in rhodium-catalyzed asymmetric oxidative coupling of biaryl compounds with alkenes, J. Am. Chem. Soc. 138(2016) 5242-5245.
(a) G. I. Shakibaei, A. Bazgir, A highly efficient one-pot synthesis of indenopyridine-fused spirocyclic systems, RSC Adv. 6(2016) 22306-22311;
(b) S. Hajra, S. Maity, S. Roy, Regioselective friedel-crafts reaction of electronrich benzenoid arenes and spiro epoxy oxindole at the spiro-centre: efficient synthesis of benzofuro indolines and 2H-spiro[benzofuran]33'-oxindoles, Adv. Synt. Catal. 358(2016) 230'-2306;
(c) A. Alizadeh, J. Mokhtari, Novel four-component route to the synthesis of spiro[indoline-34'-pyridine]-3'-carboxylate derivatives, Tetrahedron 67(2011) 3519-3523.
(a) I. Yavari, M. Nematpour, T. Damghani, Copper-catalyzed S-arylation of tetramethyl guanidine heterocumulene adducts, Tetrahedron Lett. 55(2014) 1323-1325;
(b) I. Yavari, M. Nematpour, Copper-catalyzed tandem synthesis of tetrasubstituted pyrimidines from alkynes, sulfonyl azides, trichloro acetonitrile, and tetramethyl guanidine, Synlett 24(2013) 165-168;
(c) I. Yavari, A. S. Shahvelayati, A. Malekafzali, Efficient synthesis of functionalized 24-diaminothiazoles from tetramethyl guanidine, isothiocyanates, and α-bromoketones, J. Sulf. Chem. 31(2010) 499-508;
(d) I. Yavari, A. Sheikhi, M. Nematpour, Z. Taheri, Copper-catalyzed synthesis of pentasubstituted pyridines from N-sulfonyl ketenimines, 1, 1, 3, 3-tetramethyl guanidine, and acetylene dicarboxylates, Helv. Chim. Acta 98(2015) 534-538.
(a) S. B. Azimi, J. Azizian, A green, one-pot synthesis of substituted 2, 3-dihydroquinazoline-4(1H)-ones in the presence of N-sulfonic acid pyridinium chloride, Synlett 27(2016) 1836-1839;
(b) S. B. Azimi, J. Azizian, Reaction of benzyl alcohols, isatoic anhydride, and primary amines mediated by I2/K2CO3 in water: a new and green approach for the synthesis of 2, 3-dihydroquinazolin-4(1H)-ones, Tetrahedron Lett. 57(2016) 181-184;
(c) P. Torabi, J. Azizian, J. Noei, Synthesis of benzimidazoles and benzoxazoles using TiCl3OTf in ethanol at room temperature, Tetrahedron Lett. 57(2016) 185-188.
(a) J. S. Yu, Y. L. Liu, J. Tang, X. Wang, J. Zhou, Highly efficient on water catalystfree nucleophilic addition reactions using difluoroenoxysilanes: dramatic fluorine effects, Angew. Chem. Int. Ed. 53(2014) 9512-9516;
(b) F. Zhou, X. P. Zeng, C. Wang, X. L. Zhao, J. Zhou, Organocatalytic asymmetric synthesis of 33-disubstituted oxindoles featuring two heteroatoms at the C3 position, Chem. Commun. 49(2013) 2022-2024;
(c) J. S. Yu, H. M. Huang, P. G. Ding, et al. , Catalytic enantioselective construction of sulfur-containing tetr-asubstituted carbon stereocenters, ACS Catal. 6(2016) 5319-5344.
Hongyuan Sha , Dongling Yang , Yanran Shang , Zujian Wang , Rongbing Su , Chao He , Xiaoming Yang , Xifa Long . Trithionic guanidine: A novel semi-organic short-wave ultraviolet nonlinear optical sulfate with dimeric heteroleptic tetrahedra. Chinese Chemical Letters, 2025, 36(4): 109730-. doi: 10.1016/j.cclet.2024.109730
Jindan Zhang , Zhenghong Li , Chi Li , Mengqi Zhu , Shicheng Tang , Kaicong Cai , Zhibin Cheng , Chulong Liu , Shengchang Xiang , Zhangjing Zhang . Revealing a new doping mechanism of spiro-OMeTAD with tBP participation through the introduction of radicals into HTM. Chinese Chemical Letters, 2025, 36(3): 110046-. doi: 10.1016/j.cclet.2024.110046
Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157