[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2011.32.8.2700

Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines

Ramazani, Ali (Chemistry Department, Zanjan University)
Nasrabadi, Fatemeh Zeinali (Chemistry Department, Zanjan University)
Karimi, Zahra (Chemistry Department, Zanjan University)
Rouhani, Morteza (Young Researchers Club, Zanjan Branch, Islamic Azad University)

Publication Information

Bulletin of the Korean Chemical Society / v.32, no.8, 2011 , pp. 2700-2704 More about this Journal

Abstract

The 1:1 imine intermediate generated by the addition of primary amine to chloroacetone is trapped by N-isocyaniminotriphenylphosphorane in the presence of (E)-cinnamic acids and the corresponding iminophosphorane intermediate was formed. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.

Keywords

N-Isocyaniminotriphenylphosphorane; Chloroacetone; (E)-Cinnamic acid; 1,3,4-Oxadiazole; aza-Wittig reaction;

Citations & Related Records

Times Cited By KSCI : 1 (Citation Analysis)
Times Cited By Web Of Science : 15 (Related Records In Web of Science)
Times Cited By SCOPUS : 7

1	Ramazani, A.; Ahmadi, Y.; Rouhani, M.; Shajari, N.; Souldozi, A. Heteroatom Chem. 2010, 21, 368. DOI ScienceOn
2	Ramazani, A.; Zeinali Nasrabadi, F.; Mashhadi Malekzadeh, A.; Ahmadi, Y. Monatsh Chem. 2011, 142, 625. DOI
3	Ramazani, A.; Shajari, N.; Tofangchi Mahyari, A.; Khoobi, M.; Ahmadi, Y.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2010, 185, 2496. DOI ScienceOn
4	Ramazani, A.; Shajari, N.; Mahyari, A.; Ahmadi, Y. Mol. Divers 2011, 15, 521. DOI
5	Ramazani, A.; Shajari, N.; Gouranlou, F. Phosphorus, Sulfur, Silicon Relat. Elem. 2001, 174, 223. DOI ScienceOn
6	Baxendale, I. R.; Ley, S. V.; Martinelli, M. Tetrahedron. 2005, 61, 5323. DOI ScienceOn
7	Ramazani, A.; Amini, I.; Massoudi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2006, 181, 2225. DOI ScienceOn
8	Holla, B. S.; Gonsalves, R.; Shenoy, S. Eur. J. Med. Chem. 2000, 35, 267. DOI ScienceOn
9	Chen, Q.; Zhu, X. H.; Jiang, L. L.; Liu, Z. M.; Yang, G. F. Eur. J. Med. Chem. 2008, 47, 595.
10	Coppo, F. T.; Evans, K. A.; Graybill, T. L.; Burton, G. Tetrahedron Lett. 2004, 45, 3257. DOI ScienceOn
11	Brain, C. T.; Paul, J. M.; Loong, Y.; Oakley, P. J. Tetrahedron Lett. 1999, 40, 3275. DOI ScienceOn
12	Wang, Y.; Sauer, D. R.; Djuric, S. W. Tetrahedron Lett. 2006, 47, 105. DOI ScienceOn
13	Souldozi, A.; Ramazani, A.; Bouslimani, N.; Welter, R. Tetrahedron Lett. 2007, 48, 2617. DOI ScienceOn
14	Souldozi, A.; Ramazani, A. Tetrahedron Lett. 2007, 48, 1549. DOI ScienceOn
15	Souldozi, A.; Ramazani, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2009, 184, 3191. DOI ScienceOn
16	Souldozi, A.; Ramazani, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2009, 184, 2344. DOI ScienceOn
17	Souldozi, A.; Ramazani, A. Arkivoc. 2008, Xvi, 235.
18	Souldozi, A.; lepokura, K.; Lis, T.; Ramazani, A. Z. Naturforsch. 2007, 62b, 835.
19	Ramazani, A.; Rezaei, A. Org. Lett. 2010, 12, 2852. DOI ScienceOn
20	Ramazani, A.; Shajari, N.; Mahyari, A.; Ahmadi, Y. Mol. Divers. 2011, 15, 521. DOI
21	Ramazani, A.; Rezaei, A.; Mahyari, A. T.; Rouhani, M.; Khoobi, M. Helv. Chim. Acta. 2010, 93, 2033. DOI ScienceOn
22	Ramazani, A.; Mahyari, A. Helv. Chim. Acta. 2010, 93, 2203. DOI ScienceOn
23	Ramazani, A.; Mahyari, A. T.; Rouhani, M.; Rezaei, A. Tetrahedron Lett. 2009, 50, 5625. DOI ScienceOn
24	Zeinali Nasrabadi, F.; Ramazani, A.; Ahmadi, Y. Mol. Divers. 2011, 15, DOI: 10.1007/s11030-011-9310-9. DOI
25	Domling, A. Chem. Rev. 2006, 106, 17. DOI ScienceOn
26	Ugi, I.; Werner, B.; Domling, A. Molecules. 2003, 8, 53. DOI
27	Palacios, F.; Aparicio, D.; Rubiales, G.; Alonso, C.; de los Santos, J. M. Curr. Org. Chem. 2009, 13, 810. DOI ScienceOn
28	Stolzenberg, H.; Weinberger, B.; Fehlhammer, W. P.; Pühlhofer, F. G.; Weiss, R. Eur. J. Inorg. Chem. 2005, 21, 4263.
29	Ramazani, A.; Bodaghi, A. Tetrahedron Lett. 2000, 41, 567. DOI ScienceOn
30	Pakravan, P.; Ramazani, A.; Noshiranzadeh, N.; Sedrpoushan, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2007, 182, 545. DOI ScienceOn
31	Ramazani, A.; Rahimifard, M.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2007, 182, 1. DOI ScienceOn
32	Ramazani, A.; Rahimifard, M.; Noshiranzadeh, N.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2007, 182, 413. DOI ScienceOn
33	Maleki, B.; Gholizadeh, M.; Sepehr, Z. Bull. Korean Chem. Soc. 2011, 32, 1697. DOI ScienceOn
34	Ramazani, A.; Ahmadi, E.; Kazemizadeh, A. R.; Dolatyari, L.; Noshiranzadeh, N.; Eskandari, I.; Souldozi, A. Phosphorus, Sulphur, Silicon Relat. Elem. 2005, 180, 2419. DOI ScienceOn
35	Zhu, J.; Bienayme, H. Multicomponent Reactions; Eds., Wiley: Weinheim, 2005.

9	Ali Ramazani. (2012) Phosphorus, Sulfur, and Silicon and the Related Elements -Isocyaniminotriphenylphosphorane as an Efficient Reagent for the Synthesis of Disubstituted 1,3,4-Oxadiazoles Via In-Situ Generation of Sterically Congested Iminophosphorane Derivatives / 187 (9) , 1064
1	Abdolhossain Massoudi. (2012) Bulletin of the Korean Chemical Society Four-Component Synthesis of 2-(N,N-Dialkylamino)-2,4,6-Cycloheptatrien-1-One Derivatives from Tropolone, an Isocyanide, a Primary Amine and an Aldehyde via Ugi-Smiles Coupling Reaction / 33 (1) , 39
2	Ali Ramazani. (2012) Bulletin of the Korean Chemical Society One-pot, Three-component Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (N-Isocyanoimino)triphenylphosphorane, Aromatic Carboxylic acids and (1R)-(-)-Campherchinon / 33 (2) , 453
5	Ali Ramazani. (2013) Phosphorus, Sulfur, and Silicon and the Related Elements -Wittig Reactions of in Situ Generated Iminophosphoranes / 188 (5) , 642
9	Ali Ramazani. (2013) Phosphorus, Sulfur, and Silicon and the Related Elements The Reaction of Thioacids with α-Haloketones in Water: an Environmentally Green Synthesis of Thioester Derivatives / 188 (9) , 1214
6	Ali Ramazani. (2013) Journal of Heterocyclic Chemistry The Reaction of N-Isocyaniminotriphenylphosphorane with 2-Oxopropylbenzoate (or 4-Bromobenzoate) and a Primary Amine in the Presence of (E)-Cinnamic Acid Derivatives: A One-Pot Efficient Four-Component Reaction for the Synthesis of 2-(Arylamino)-2-(5-aryl / 50 (6) , 1294
7	Ali Reza Kazemizadeh. (2016) Journal of the Iranian Chemical Society Synthesis and anti-brucella activity of some new 1,3,4-oxadiazole derivatives containing a ferrocene unit / 13 (7) , 1349
12	Morteza Rouhani. (2011) Bulletin of the Korean Chemical Society Very Efficient and Rapid Catalyst-free One-pot Three Component Synthesis of 2,5-Dihydro-5-imino-2-methylfuran-3,4-dicarboxylate Derivatives Under Ultrasound Irradiation / 33 (12) , 4127
3	(2018) Journal of Structural Chemistry Molecular Structure, Electronic Properties, Homo–Lumo, MEP and NBO Analysis of (N-Isocyanimino) Triphenylphosphorane (Ph3PNNC): DFT Calculations / 59 (3) , 529
11	Ali Ramazani. (2011) Bulletin of the Korean Chemical Society Four-Component Preparation of Disubstituted 1,3,4-Oxadiazoles from (N-isocyanimino)triphenylphosphorane, Phenylacetylenecarboxylic Acid, Biacetyl and Primary Amines / 33 (11) , 3701
5	JAVAD SAFAEI-GHOMI. (2011) Journal of chemical sciences The reaction of carbon disulphide with α-haloketones and primary amines in the presence of potassium iodide as catalyst / 125 (5) , 1087
7	Hamideh Ahankar. (2011) Phosphorus, sulfur, and silicon and the related elements N-Isocyaniminotriphenylphosphorane (Ph3PNNC) as an Efficient Reagent for the Synthesis of Fully Substituted 1,3,4-Oxadiazoles from 3-Phenyl-2-Propynoic Acid, Secondary Amines and Aromatic Bis-Aldehyde / 188 (7) , 886
1	Morteza Rouhani. (2011) Ultrasonics sonochemistry Novel, fast and efficient one-pot sonochemical synthesis of 2-aryl-1,3,4-oxadiazoles / 21 (1) , 262
2	Ping He. (2011) Bulletin of the Korean Chemical Society Efficient and Selective Construction of Pyrrolo[3,2-d]pyrimidine Derivatives / 35 (2) , 617
12	ALI RAMAZANI. (2015) Journal of chemical sciences Synthesis of N-acylurea derivatives from carboxylic acids and N,N′-dialkyl carbodiimides in water / 127 (12) , 2269
1	Ali Ramazani. (2011) Phosphorus, sulfur, and silicon and the related elements Ultrasound-Promoted Three-Component Reaction of <I>N</I>-isocyaniminotriphenyl-phosphorane, (<I>E</I>)-cinnamic Acids, and Biacetyl / 190 (1) , 20
None	Ali Ramazani. (2016) Ultrasonics sonochemistry Catalyst-free sonosynthesis of highly substituted propanamide derivatives in water / 28 (None) , 393
1	(2020) Monatshefte für Chemie Pseudo-three-component synthesis of substituted 1,2,4-triazolo[1,5-a]pyridines / 151 (1) , 93
4	(2011) Organic & biomolecular chemistry Syntheses and medicinal chemistry of azepinoindolones: a look back to leap forward / 19 (4) , 738
7	(2011) Phosphorus, sulfur, and silicon and the related elements Investigation of the reaction mechanism between cyclohexyl isocyanide and dimethyl acetylenedicarboxylate in the presence of 2-mercaptobenzoxazole: a theoretical study / 196 (7) , 656

1	Four-Component Synthesis of 2-(N,N-Dialkylamino)-2,4,6-Cycloheptatrien-1-One Derivatives from Tropolone, an Isocyanide, a Primary Amine and an Aldehyde via Ugi-Smiles Coupling Reaction / [Massoudi, Abdolhossain;Amini, Issa;Ramazani, Ali;Nasrabadi, Fatemeh Zeinali;Ahmadi, Yavar;] / Bulletin of the Korean Chemical Society
2	One-pot, Three-component Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (N-Isocyanoimino)triphenylphosphorane, Aromatic Carboxylic acids and (1R)-(-)-Campherchinon / [Ramazani, Ali;Nasrabadi, Fatemeh Zeinali;Abdian, Behnaz;Rouhani, Morteza;] / Bulletin of the Korean Chemical Society
3	Four-Component Preparation of Disubstituted 1,3,4-Oxadiazoles from (N-isocyanimino)triphenylphosphorane, Phenylacetylenecarboxylic Acid, Biacetyl and Primary Amines / [Ramazani, Ali;Abdian, Behnaz;Nasrabadi, Fatemeh Zeinali;Shajari, Nahid;Ranjdoost, Zahra;] / Bulletin of the Korean Chemical Society
4	Very Efficient and Rapid Catalyst-free One-pot Three Component Synthesis of 2,5-Dihydro-5-imino-2-methylfuran-3,4-dicarboxylate Derivatives Under Ultrasound Irradiation / [Rouhani, Morteza;Ramazani, Ali;Joo, Sang Woo;Hanifehpour, Younes;] / Bulletin of the Korean Chemical Society

1	/ Turkish Journal of Chemistry
2	/ Turkish Journal of Chemistry