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Journal articles on the topic 'N,S-acetals'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Schuijl, P. J. W., H. J. T. Bos, and L. Brandsma. "Ketene S,N-acetals from thioamides." Recueil des Travaux Chimiques des Pays-Bas 87, no. 1 (2010): 123–25. http://dx.doi.org/10.1002/recl.19680870116.

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2

Junjappa, H., H. Ila та C. V. Asokan. "α-Oxoketene-S,S-, N,S- and N,N-acetals: Versatile intermediates in organic synthesis". Tetrahedron 46, № 16 (1990): 5423–506. http://dx.doi.org/10.1016/s0040-4020(01)87748-6.

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3

TAKAHATA, HIROKI, TOMOKO NAKAJIMA, MASAHARU NAKANO, AKIRA TOMIGUCHI, and TAKAO YAMAZAKI. "Ketene-S,N-acetals as synthetic intermediates for heterocycles. Reaction of ketene-S,N-acetals with aryl isocyanates." CHEMICAL & PHARMACEUTICAL BULLETIN 33, no. 10 (1985): 4299–308. http://dx.doi.org/10.1248/cpb.33.4299.

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4

Mathews, Annie, E. R. Anabha, and C. G. Sholly. "A Facile Method for the Synthesis of Oxoketene-N,S- and -N,N-acetals from Reactions of Amino Compounds." Organic Chemistry International 2010 (November 28, 2010): 1–5. http://dx.doi.org/10.1155/2010/396020.

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2-Aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes reacted with various primary amines, namely, o-phenylenediamine, ethylenediamine, and anilines to produce functionalized oxoketene-N,S-acetals and N,N-acetals in good yields. Imidazolo derivatives synthesized with o-phenylenediamine and ethylenediamine containing a formyl group could act as valuable starting materials for a variety of substituted heterocyclic compounds.

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5

Rudoref, Wolf-Dieter, Jens Köditz, Nadja Henze, and Ani Tersakian. "REACTIONS OF ACYLFORMYLKETENE S,S-AND S,N-ACETALS WITH AMINES." Phosphorus, Sulfur, and Silicon and the Related Elements 107, no. 1-4 (1995): 87–97. http://dx.doi.org/10.1080/10426509508027924.

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6

Hojo, Masaru, Ryōichi Masuda, Etsuji Okada, Hiromi Yamamoto, Katsushi Morimoto та Ken Okada. "Facile Synthesis of β-TrifluoroacetylketeneO,N-,S,N- andN,N-Acetals". Synthesis 1990, № 03 (1990): 195–98. http://dx.doi.org/10.1055/s-1990-26827.

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7

OTTEN, P. A., N. OSKAM, and A. VAN DER GEN. "ChemInform Abstract: A Horner-Wittig Approach to S,N-Ketene Acetals. Acid-Catalyzed Hydrolysis of S,N-Ketene Acetals to (S)-Thioesters." ChemInform 27, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199650075.

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8

Zhang, Lin, Jinhuan Dong, Xianxiu Xu, and Qun Liu. "Chemistry of Ketene N,S-Acetals: An Overview." Chemical Reviews 116, no. 2 (2016): 287–322. http://dx.doi.org/10.1021/acs.chemrev.5b00360.

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9

Kirkeby, Emily K., and Andrew G. Roberts. "Design, synthesis and characterization of structurally dynamic cyclic N,S-acetals." Chemical Communications 56, no. 64 (2020): 9118–21. http://dx.doi.org/10.1039/d0cc03503c.

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10

El-Saghier, Ahmed M. M., Mansour A. Makhlouf, Naglaa F. H. Mahmoud, and Wedad A. El-Adawish. "A-Alkenoyl Ketene S,S- and N,S-Acetals As Starting For Unexpected and Novel Synthesis of N-Heterocycles." JOURNAL OF ADVANCES IN CHEMISTRY 6, no. 1 (2010): 861–72. http://dx.doi.org/10.24297/jac.v6i1.965.

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A series of N-heterocycles such as diazaspiro-[4.5]decane, pyrazolo[4,3-d][1,2]-diazepine, imidazo[3,2,1ij][1,8]naphthyridine derivatives or pyrazolo[3,4-b]pyridin-4-ol were synthesized using a-alkenoyl-, a,a-dialkenoyl ketene-(S,S)-acetals 2a-d, 3a-c or a-dialkenoyl ketene-(N,S)-acetal 12 as starting materials. The biological activity of some new synthesized compounds have been investigated.

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11

Somogyi, László. "Synthesis, Oxidation and Dehydro- genation of Cyclic N,O- and N,S-Acetals. Part 1. Transformation of N,S-Acetals: 3-Acyl-1,3,4-thiadiazolines." HETEROCYCLES 63, no. 10 (2004): 2243. http://dx.doi.org/10.3987/com-04-10137.

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12

Reddy, T. Indrasena, Baburao M. Bhawal, and Srinivasachari Rajappa. "Unique zeolite-catalyzed synthesis of nitroketene S,N-acetals." Tetrahedron 49, no. 10 (1993): 2101–8. http://dx.doi.org/10.1016/s0040-4020(01)86309-2.

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13

Otten, Pieter A., Njord Oskam, and Arne van der Gen. "A Horner-Wittig approach to S,N-ketene acetals." Tetrahedron 52, no. 33 (1996): 11095–104. http://dx.doi.org/10.1016/0040-4020(96)00626-6.

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14

Mykhaylychenko, Sergiy S., Jean-Philippe Bouillon, and Yuriy G. Shermolovich. "Oxidation and chlorination reactions of perfluoroketene-N,S-acetals." Journal of Fluorine Chemistry 130, no. 10 (2009): 878–85. http://dx.doi.org/10.1016/j.jfluchem.2009.06.019.

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15

Loghmani-Khouzani, H., M. M. Sadeghi та M. H. Ghorbani. "A convenient synthesis of some α-oxoketene-N,S- and N,N-acetals". Journal of the Iranian Chemical Society 3, № 4 (2006): 360–66. http://dx.doi.org/10.1007/bf03245959.

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16

Suć, Josipa, Irena Dokli, and Matija Gredičak. "Chiral Brønsted acid-catalysed enantioselective synthesis of isoindolinone-derived N(acyl),S-acetals." Chemical Communications 52, no. 10 (2016): 2071–74. http://dx.doi.org/10.1039/c5cc08813e.

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17

Liu, Jinying, Xiaolan Fu, Yang Zhou, Guangyuan Zhou, Yongjiu Liang та Dewen Dong. "A Facile and Divergent Synthesis of Substituted Pyridine-2,4(1H,3H)-diones and 4H-Thiopyran-4-ones from α-Alkenoyl-α-carbamoyl Ketene-S,S-acetals". Australian Journal of Chemistry 63, № 8 (2010): 1267. http://dx.doi.org/10.1071/ch09489.

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A facile and divergent synthesis of substituted pyridine-2,4(1H,3H)-diones and 4H-thiopyran-4-ones from readily available α-alkenoyl-α-carbamoyl ketene-S,S-acetals has been developed. Subjected to N,N-dimethylformamide at 125°C, α-alkenoyl-α-carbamoyl ketene-S,S-acetals underwent an intramolecular aza-nucleophilic vinyl substitution reaction, a formal [5C + 1N] annulation, to give the corresponding substituted pyridine-2,4(1H,3H)-diones in high yields, whereas in the presence of Na2S·9H2O in DMF at 75°C, tandem intermolecular and intramolecular thia-nucleophilic vinyl substitution reactions, a

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18

Zhou, Aihua, and Charles U. Pittman. "Aryl radical cyclizations of N-(2-halobenzoyl)-cyclic ketene-N,S-acetals." Tetrahedron Letters 46, no. 22 (2005): 3801–5. http://dx.doi.org/10.1016/j.tetlet.2005.03.205.

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19

Cai, Yan, Haihong Ge, Weize Sun, and Zhiwei Miao. "Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers." Synthesis 47, no. 11 (2015): 1669–77. http://dx.doi.org/10.1055/s-0034-1380384.

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The trifluoroborane-catalyzed C–H functionalization/S–H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.

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20

Huang, Fei, Ping Wu, Liandi Wang, Jiping Chen, Chenglin Sun та Zhengkun Yu. "Copper-mediated intramolecular oxidative C–H/N–H cross-coupling of α-alkenoyl ketene N,S-acetals to synthesize pyrrolone derivatives". Chem. Commun. 50, № 83 (2014): 12479–81. http://dx.doi.org/10.1039/c4cc05837b.

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CuCl<sub>2</sub> and CuBr<sub>2</sub>-mediated intramolecular oxidative C–H/N–H cross-coupling/halogenation of β-thioalkyl-α-alkenoyl ketene N,S-acetals provides a new concise synthetic route to pyrrolones.

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21

DOROKHOV, V. A., A. V. KOMKOV, and V. S. BOGDANOV. "ChemInform Abstract: Heterocyclization of Acetylketene N,S-Acetals with Benzoylcyanamide." ChemInform 29, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199811169.

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22

Altenbach, Hans-Josef, Peter R. Roth, and David J. Brauer. "Synthesis of epimeric pure spiro N,S-acetals ofL-menthone." Liebigs Annalen 1995, no. 8 (1995): 1427–31. http://dx.doi.org/10.1002/jlac.1995199508193.

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23

Razavi, Zohreh Sahhaf, Mohammad Bayat, and Hajar Hosseini. "Synthesis of highly functionalized thiazolo[3,2-a]pyridine derivatives via a five-component cascade reaction based on nitroketene N,S-acetal." RSC Advances 10, no. 52 (2020): 31039–48. http://dx.doi.org/10.1039/d0ra03910a.

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24

Bonacorso, Helio G., Renata P. Vezzosi, Isadora R. Rodrigues, et al. "Preparation of novel trifluoroacetylketene O,N-acetals and trifluoromethyl-containing S,S-sulfoximido N-substituted heterocycles." Journal of the Brazilian Chemical Society 20, no. 7 (2009): 1370–78. http://dx.doi.org/10.1590/s0103-50532009000700024.

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25

Goasdoue, Claude, and Marcel Gaudemar. "S-silyketene s,n-acetals. cross-aldol type condensation reaction with schiff bases." Tetrahedron Letters 26, no. 8 (1985): 1015–18. http://dx.doi.org/10.1016/s0040-4039(00)98500-9.

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26

Chanu, Langpoklakpam Gellina, Okram Mukherjee Singh, Sang-Hun Jang, and Sang-Gyeong Lee. "Regioselective Synthesis of Heterocyclic Ketene N,N-, N,O- and N,S-acetals in Aqueous Medium." Bulletin of the Korean Chemical Society 31, no. 4 (2010): 859–62. http://dx.doi.org/10.5012/bkcs.2010.31.04.859.

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27

Elgemeie, Galal H., Ahmed H. Elghandour, and Ghada W. Abd Elaziz. "Novel Synthesis of Heterocyclic Ketene N,N-, N,O-, and N,S-Acetals Using Cyanoketene Dithioacetals." Synthetic Communications 33, no. 10 (2003): 1659–64. http://dx.doi.org/10.1081/scc-120018927.

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28

Albuquerque, Tábata B., Caren D. G. da Silva, Aline R. de Oliveira, et al. "Lipase catalyzed 1,2-addition of thiols to imines under mild conditions." New Journal of Chemistry 42, no. 3 (2018): 1642–45. http://dx.doi.org/10.1039/c7nj03387g.

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29

Beard, Debbie J., Sumer A. Barakat, Nathanael B. Lockhart, et al. "Four-membered ring cyclic ketene –O,O–, –O,S–, –O,N–, –S,S–, –S,N–, and –N,N–acetals and their corresponding cations: a computational study." Structural Chemistry 23, no. 2 (2011): 351–57. http://dx.doi.org/10.1007/s11224-011-9869-x.

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30

Somogyi, László. "Synthesis, oxidation and dehydrogenation of cyclic N,O- and N,S-acetals. Part III. Transformation of N,O-acetals: 3-acyl-1,3,4-oxadiazolines." Journal of Heterocyclic Chemistry 44, no. 6 (2007): 1235–46. http://dx.doi.org/10.1002/jhet.5570440603.

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31

Kim, Jun Ki, Hwan Jung Lim, Kyung Chae Jeong, and Seong Jun Park. "One-pot sequential synthesis of tetrasubstituted thiophenes via sulfur ylide-like intermediates." Beilstein Journal of Organic Chemistry 14 (January 26, 2018): 243–52. http://dx.doi.org/10.3762/bjoc.14.16.

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Herein, we describe a novel approach for the practical synthesis of tetrasubstituted thiophenes 8. The developed method was particularly used for the facile preparation of thienyl heterocycles 8. The mechanism for this reaction is based on the formation of a sulfur ylide-like intermediate. It was clearly suggested by (i) the intramolecular cyclization of ketene N,S-acetals 7 to the corresponding thiophenes 8, (ii) 1H NMR studies of Meldrum’s acid-substituted aminothioacetals 9, and (iii) substitution studies of the methoxy group on Meldrum’s acid containing N,S-acetals 9b. Notably, in terms of

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32

Takahata, Hiroki, Keiko Moriyama, Akira Anazawa, Tomoko Nakajima, Yasunori Banba, and Takao Yamazaki. "Synthesis of Nitrogen- and Oxygen-heterocycles Using Ketene-S,N-acetals." HETEROCYCLES 24, no. 1 (1986): 228. http://dx.doi.org/10.3987/r-1986-01-0228.

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33

Takahata, Hiroki, Kyoko Yamabe, and Takao Yamazaki. "Lithio-ketene-S,N-acetals: New Synthesis of Multifunctionalized 2-Pyridones." Synthesis 1986, no. 12 (1986): 1063–65. http://dx.doi.org/10.1055/s-1986-31878.

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34

Marcelis, Antonius T. M., and Henk C. Van Der Plas. "Cycloaddition reactions of cyclic ketene-N,S-acetals with 1,2,4,5-tetrazines." Journal of Heterocyclic Chemistry 24, no. 3 (1987): 545–48. http://dx.doi.org/10.1002/jhet.5570240302.

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35

REDDY, T. I., B. M. BHAWAL, and S. RAJAPPA. "ChemInform Abstract: Unique Zeolite-Catalyzed Synthesis of Nitroketene S,N-Acetals." ChemInform 24, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199326208.

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36

Sokolova, E. A., A. E. Tsil'ko, and I. A. Maretina. "Synthesis of dienic N,S-ketene acetals of the pyrimidine series." Chemistry of Heterocyclic Compounds 26, no. 11 (1990): 1284–85. http://dx.doi.org/10.1007/bf00476987.

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37

Hebishy, Ali M. S., Galal H. Elgemeie, and Ahmed H. M. Elwahy. "Novel Bis(2‐cyanoketene‐ S , S ‐/ S , N ‐acetals): Versatile Precursors for Novel Bis(aminopyrazole) Derivatives." Journal of Heterocyclic Chemistry 56, no. 5 (2019): 1581–87. http://dx.doi.org/10.1002/jhet.3536.

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38

Surya Prakash Rao, H., and A. Parthiban. "One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines." Org. Biomol. Chem. 12, no. 32 (2014): 6223–38. http://dx.doi.org/10.1039/c4ob00628c.

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Pseudo three-component condensation of aliphatic/aromatic/α,β-unsaturated aldehydes and nitroketene-N,S-acetals to afford diversely functionalized hexa-substituted 1,4-dihydropyridines under 2-aminopyridine catalysis was achieved.

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39

Jordão, Alessandro K., Juliana Novais, Bruno Leal, et al. "Synthesis using microwave irradiation and antibacterial evaluation of new N,O-acetals and N,S-acetals derived from 2-amino-1,4-naphthoquinones." European Journal of Medicinal Chemistry 63 (May 2013): 196–201. http://dx.doi.org/10.1016/j.ejmech.2013.01.010.

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40

Srivastava, Abhijeet, Gaurav Shukla, Anugula Nagaraju та ін. "In(OTf)3-catalysed one-pot versatile pyrrole synthesis through domino annulation of α-oxoketene-N,S-acetals with nitroolefins". Org. Biomol. Chem. 12, № 29 (2014): 5484–91. http://dx.doi.org/10.1039/c4ob00781f.

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An operationally simple and efficient one-pot direct access to pyrroles has been achieved by annulation of α-oxoketene-N,S-acetals with β-nitrostyrenes catalyzed by In(OTf)<sub>3</sub>under solvent-free conditions.

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41

Yamazaki, Takao, Hiroki Takahata, Yasunori Banba, and Mayumi Mozumi. "Regioselective Thio-Claisen Rearrangement via S-Allyl Ketene-S,N-acetals Generated from Cyclic S-Allylmonothiodicarboximide Salts." HETEROCYCLES 24, no. 12 (1986): 3347. http://dx.doi.org/10.3987/r-1986-12-3347.

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42

Gordeev, M. F., A. V. Komkov, and V. A. Dorokhov. "Synthesis of pyrimidines and pyrido[2,3-d]pyrimidines using N,S- and N,N-acetals of diacetylketene." Chemistry of Heterocyclic Compounds 26, no. 9 (1990): 1075–76. http://dx.doi.org/10.1007/bf00472498.

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43

Zhou, Aihua, Moses N. Njogu, and Charles U. Pittman. "Stereoselective radical cyclizations of N-(2-halobenzoyl)-cyclic ketene-N,X(X=O, S)-acetals." Tetrahedron 62, no. 17 (2006): 4093–102. http://dx.doi.org/10.1016/j.tet.2006.02.018.

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44

Luo, Shao-Xiong, Yanzhou Liu, Michael J. Lambrecht та ін. "cis-Selective synthesis of 1,3-disubstituted tetrahydro-β-carbolines from N-sulfonyl N,S-acetals". Organic & Biomolecular Chemistry 17, № 43 (2019): 9510–13. http://dx.doi.org/10.1039/c9ob01796h.

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45

Zhou, Aihua, and Charles U. Pittman. "Reactions of 2-methylthiazolines and N-methyl cyclic ketene-N,S-acetals with acid chlorides." Tetrahedron Letters 45, no. 48 (2004): 8899–903. http://dx.doi.org/10.1016/j.tetlet.2004.09.182.

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46

Dorokhov, Vladimir, Alexander Komkov, and Sergey Baranin. "Diacetylketene N,S-acetals in synthesis of new functionalized 2(1H)-pyrimidinethiones." Arkivoc 2003, no. 14 (2003): 178–86. http://dx.doi.org/10.3998/ark.5550190.0004.e17.

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47

Manjunatha, Sulur G., K. Venodhar Reddy, and Srinivasachari Rajappa. "Nitroketene-s,n-acetals as precursors for nitroacetamides and the elusive nitrothioacetahides." Tetrahedron Letters 31, no. 9 (1990): 1327–30. http://dx.doi.org/10.1016/s0040-4039(00)88798-5.

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48

Sommen, Geoffroy, Alain Comel, and Gilbert Kirsch. "Preparation of thieno[2,3-b]pyrroles starting from ketene-N,S-acetals." Tetrahedron 59, no. 9 (2003): 1557–64. http://dx.doi.org/10.1016/s0040-4020(03)00054-1.

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49

Murai, Toshiaki, Kozue Fukushima, Yukiyasu Ohta, and Yuichiro Mutoh. "Syntheses and Stability of Alkynyl S,N-Acetals Derived from 2-Propynals." Phosphorus, Sulfur, and Silicon and the Related Elements 184, no. 6 (2009): 1462–80. http://dx.doi.org/10.1080/10426500902947765.

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50

Shawali, Ahmad S., Abdelwahed R. Sayed, and Mohie M. Zayed. "Site selectivity in reactions of hydrazonoyl halides with ketene-N,S-acetals." Journal of Sulfur Chemistry 29, no. 5 (2008): 521–27. http://dx.doi.org/10.1080/17415990802105580.

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