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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 20
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Original Articles

Synthesis of New 2-Aryl Substituted 2,3-Dihydroquinazoline-4(1H)-ones Under Solvent-Free Conditions, Using Molecular Iodine as a Mild and Efficient Catalyst

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Pages 3567-3576 | Received 05 Feb 2008, Published online: 29 Sep 2008

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Read on this site (6)

Sajjad Azizi, Jafar Soleymani & Mohammad Hasanzadeh. (2020) KCC-1/Pr-SO3H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one. Nanocomposites 6:1, pages 31-40.
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Ramamohan Mekala, M. V. Madhubabu, G. Dhanunjaya, Sridhar Regati, K. B. Chandrasekhar & Jayaprakash Sarva. (2017) Efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by titanium silicon oxide nanopowder in aqueous media. Synthetic Communications 47:2, pages 121-130.
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Samir Y. Abbas, Khairy A. M. El-Bayouki & Wahid M. Basyouni. (2016) Utilization of isatoic anhydride in the syntheses of various types of quinazoline and quinazolinone derivatives. Synthetic Communications 46:12, pages 993-1035.
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Suhui Wang, Shan Yin, Sheng Xia, Yanhui Shi, Shujiang Tu & Liangce Rong. (2012) An efficient synthesis of 3-benzylquinazolin-4(1H)-one derivatives under catalyst-free and solvent-free conditions. Green Chemistry Letters and Reviews 5:4, pages 603-607.
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Shahnaz Rostamizadeh, Ali Mohammad Amani & Nasrin Shadjou. (2012) Silica Phosphoric Acid (SPA) as a Highly Active, Reusable, Heterogeneous Catalyst for the Synthesis of 2-Amino/Anilino-5-ARYL-1,3,4-Thiadiazine Bromide Derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements 187:2, pages 238-244.
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Jitender M. Khurana & Sanjay Kumar. (2011) An efficient, catalyst free synthesis of 3-(2′'-benzothiazolyl)-2,3-dihydroquinazolin-4(1H)-ones in aqueous medium. Green Chemistry Letters and Reviews 4:4, pages 321-325.
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Articles from other publishers (66)

Amir Samiei, Mohammad Ali Bodaghifard & Mahdia Hamidinasab. (2024) Green and Convenient Synthesis of Pharmaceutically Active Mono and Bis-dihydroquinazolines via a One-pot Multicomponent Reaction Under Sulfamic Acid Catalysis. Current Green Chemistry 11:2, pages 194-200.
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Issa Yavari, Somayeh Akbarzadeh & Meysam Ghorbanzadeh. (2024) Formation of quinazolin-4(3H)-ones from N-sulfonoketenimines and 2-aminobenzamides. Journal of the Iranian Chemical Society 21:4, pages 1011-1019.
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Zahra Baymaninezhad, Haman Tavakkoli, Seyyed Jafar Saghanezhad & Elham Tahanpesar. (2023) Melamine-terephthalaldehyde covalent organic framework-copper-tetrabenzenecarboxylic acid metal organic framework (COF–MOF): an efficient heterogeneous acidic catalyst for the one-pot preparation of 2,3-dihydroquinazoline-4(1H)-one derivatives. Research on Chemical Intermediates 49:11, pages 5101-5119.
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Aayushi Lodhi, Ajay K Dalai & Kalpana C Maheria. (2023) Environmentally benign synthesis of quinazoline-based heterocyclic compounds over zeolite H-BEA catalyst with bimodal porosity. Journal of Chemical Sciences 135:2.
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Akshay Pandurang Gurav, Rutikesh Pandit Gurav, Rutuja Ramesh Zond, Nayak Devappa Satyanarayan, Nippu Ningegowda Belur & Shankar Poshatti Hangirgekar. (2023) Design and synthesis of γ‐Fe 2 O 3 @Ag‐S‐CH 2 ‐COOH nanocatalyst for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1 H )‐ones and their anti‐skin cancer activity . Applied Organometallic Chemistry 37:6.
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Navjeet Kaur. 2023. Iodine-Assisted Synthesis of Six- and Seven-Membered Heterocycles. Iodine-Assisted Synthesis of Six- and Seven-Membered Heterocycles 89 124 .
Vanessza Judit Kolcsár & György Szőllősi. (2022) Synthesis of a Pyrrolo[1,2-a]quinazoline-1,5-dione Derivative by Mechanochemical Double Cyclocondensation Cascade. Molecules 27:17, pages 5671.
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Mohsen Bakhtiarian & Mohammad Mehdi Khodaei. (2022) Synthesis of 2,3-dihydro-4(1 H) quinazolinones using a magnetic pectin-supported deep eutectic solvent. Colloids and Surfaces A: Physicochemical and Engineering Aspects 641, pages 128569.
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Nishtman Hassanloie, Nader Noroozi Pesyan, Golaleh Sheykhaghaei & Khadijeh Ojaghi Aghbash. (2021) Anchoring of Cu–dimethylglyoxime complex in MCM-41 matrix: a new, recyclable, and highly efficient nanocatalyst for the green preparation of 2,3-dihydroquinazolin-4(1H)-ones. Monatshefte für Chemie - Chemical Monthly 152:7, pages 833-844.
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Sutthichat Kerdphon, Jira Jongcharoenkamol, Jaruwan Chatwichien, Thishana Singh, Duangdao Channei, Vachira Choommongkol, Puracheth Rithchumpon & Puttinan Meepowpan. (2021) Microwave‐Assisted Green Synthesis of 2,3‐Dihydroquinazolinones under Base‐ and Catalyst‐Free conditions. ChemistrySelect 6:19, pages 4661-4669.
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Mohamed El Haimer, Márta Palkó, Matti Haukka, Márió Gajdács, István Zupkó & Ferenc Fülöp. (2021) Synthesis and biological evaluation of the new ring system benzo[ f ]pyrimido[1,2- d ][1,2,3]triazolo[1,5- a ][1,4]diazepine and its cycloalkane and cycloalkene condensed analogues . RSC Advances 11:12, pages 6952-6957.
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Bijeta Mitra, Gyan Chandra Pariyar & Pranab Ghosh. (2021) β-Cyclodextrin: a supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1 H )-one . RSC Advances 11:3, pages 1271-1281.
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Nader Noroozi Pesyan, Aria Danandeh Asl & Shadi Namdar. (2020) A novel magnetic nanocatalyst Fe 3 O 4 @PEG–Ni for the green synthesis of 2,3‐dihydroquinazolin‐4(1 H )‐ones . Applied Organometallic Chemistry 34:8.
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Gyan Chandra Pariyar, Bijeta Mitra, Suvodip Mukherjee & Pranab Ghosh. (2020) Ascorbic Acid as an Efficient Organocatalyst for the Synthesis of 2‐Substituted‐2,3‐dihydroquinazolin‐4(1 H )‐one and 2‐Substituted Quinazolin‐4(3 H )‐one in Water . ChemistrySelect 5:1, pages 104-108.
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Hossein Ghafuri, Nahal Goodarzi, Afsaneh Rashidizadeh & Mohammad Ali Douzandegi Fard. (2019) ompg-C3N4/SO3H: an efficient and recyclable organocatalyst for the facile synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Research on Chemical Intermediates 45:10, pages 5027-5043.
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Zahra Tashrifi, Mohammad Mohammadi-Khanaposhtani, Mahmood Biglar, Bagher Larijani & Mohammad Mahdavi. (2019) Isatoic Anhydride: A Fascinating and Basic Molecule for the Synthesis of Substituted Quinazolinones and Benzo di/triazepines. Current Organic Chemistry 23:10, pages 1090-1130.
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Chuanhuan Chen, A. Xuejiao, Xia Li, Guoli Huang & Bo Liu. (2019) Phosphomolybdic Acid (PMA)-catalyzed One-pot Synthesis of 2,3- Dihydroquinazolines. Letters in Organic Chemistry 16:8, pages 683-687.
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Michael Aalinejad, Nader Noroozi Pesyan, Nosrat Heidari, Hana Batmani & Aria Danandeh Asl. (2019) Supramolecular Fe 3 O 4 @PEG/−diaza crown ether@Ni: a novel magnetically reusable nano catalyst for the clean synthesis of 2‐aryl‐2,3‐dihydroquinazolin‐4(1 H )‐ones . Applied Organometallic Chemistry 33:6.
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Akram Fakhri, Ali Naghipour & Zahra Haji Ghasemi. (2018) Catalytic performance of tannic acid-SO3H supported on Fe3O4@SiO2 nanoparticles for synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Solid State Sciences 83, pages 107-114.
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Hamid Reza Safaei, Mohsen Shekouhy & Somayeh Ghorbanzadeh. (2018) Polyethylene Glycol‐Bonded Tetraethyl Ammonium Hydroxide ([PEG‐TEA]OH): A New Surfactant‐Combined Base Catalyst for the Synthesis of 2,3‐Dihydroquinazolin‐4(1 H )‐ones in Water . ChemistrySelect 3:17, pages 4750-4759.
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Taiebeh Tamoradi, Arash Ghorbani-Choghamarani & Mohammad Ghadermazi. (2018) Synthesis of a new Pd(0)-complex supported on magnetic nanoparticles and study of its catalytic activity for Suzuki and Stille reactions and synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives. Polyhedron 145, pages 120-130.
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Carla E. Brown, Tiffany Kong, Claudia Bordón, Robert Yolken, Lorraine Jones-Brando & James McNulty. (2018) One-pot, multicomponent synthesis of 2,3-disubstituted quinazolin-ones with potent and selective activity against Toxoplasma gondii. Bioorganic & Medicinal Chemistry Letters 28:9, pages 1642-1646.
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Hana Batmani, Nader Noroozi Pesyan & Forugh Havasi. (2018) Ni-Biurea complex anchored onto MCM-41: As an efficient and recyclable nanocatalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Microporous and Mesoporous Materials 257, pages 27-34.
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Mariateresa Badolato, Francesca Aiello & Nouri Neamati. (2018) 2,3-Dihydroquinazolin-4(1 H )-one as a privileged scaffold in drug design . RSC Advances 8:37, pages 20894-20921.
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Carla E. Brown, Tiffany Kong, James McNulty, Leonardo D'Aiuto, Kelly Williamson, Lora McClain, Paolo Piazza & Vishwajit L. Nimgaonkar. (2017) Discovery of potent antiviral (HSV-1) quinazolinones and initial structure-activity relationship studies. Bioorganic & Medicinal Chemistry Letters 27:20, pages 4601-4605.
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Mahesh Kancherla & Vijayakumar Badathala. (2017) Aluminium exchanged Indian clay as an efficient reusable green catalyst for synthesis of 2, 3-dihydroquinazolin-4(1H)-one derivatives. Journal of Porous Materials 24:5, pages 1187-1196.
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Chetan K. Khatri, Manisha S. Patil & Ganesh U. Chaturbhuj. (2017) Sulfated polyborate: mild, efficient and eco-friendly catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Journal of the Iranian Chemical Society 14:8, pages 1683-1689.
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Lotfi Shiri & Mosstafa Kazemi. (2017) Magnetic Fe3O4 nanoparticles supported amine: a new, sustainable and environmentally benign catalyst for condensation reactions. Research on Chemical Intermediates 43:8, pages 4813-4832.
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Shrikrishna Karhale, Dattatray Survase, Rahul Bhat, Panchsheela Ubale & Vasant Helavi. (2017) A practical and green protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones using oxalic acid as organocatalyst. Research on Chemical Intermediates 43:7, pages 3915-3924.
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Abdul Ashik Khan, Kanchan Mitra, Abhijit Mandal, Nabajyoti Baildya & Mohabul A. Mondal. (2017) Yttrium nitrate catalyzed synthesis, photophysical study, and TD‐DFT calculation of 2,3‐dihydroquinazolin‐4(1H)‐ones. Heteroatom Chemistry 28:4.
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Archi Sharma, Satish Gudala, Srinivasa Rao Ambati, Santhosh Penta, Shyama Prasad Mahapatra, Rajeswar Rao Vedula, Someshwar Pola & Bibhudendra Acharya. (2017) Synthesis of Heterocyclic Compounds Catalyzed by Metal/Metal Oxide-Multiwall Carbon Nanotube Nanocomposites. Journal of the Chinese Chemical Society 64:6, pages 589-606.
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Seyedeh Yasaman Afsar, Ghodsi Mohammadi Ziarani, Hoda Mollabagher, Parisa Gholamzadeh, Alireza Badiei & Ali Abolhasani Soorki. (2016) Application of SBA-Pr-SO3H in the synthesis of 2,3-dihydroquinazoline-4(1H)-ones: characterization, UV–Vis investigations and DFT studies. Journal of the Iranian Chemical Society 14:3, pages 577-583.
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Ramin Ghorbani-Vaghei, Azadeh Shahriari, Yaser Maghbooli & Jafar Mahmoudi. (2016) Efficient synthesis of novel quinazoline-4(1H)-one derivatives by N-halosulfonamides. Research on Chemical Intermediates 43:2, pages 983-993.
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K. Kumar G. Ramakrishna, Ravi Kumar Thakur, Venkata Reddy Pasam, Jyotsana Pandey, Rohit Mahar, Sanjeev K. Shukla, Akhilesh K. Tamrakar & Rama Pati Tripathi. (2017) Synthesis of novel glycosyl-1,2,3-1H-triazolyl methyl quinazolin-4(3H)-ones and their effect on GLUT4 translocation. Tetrahedron 73:2, pages 187-203.
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Javad Safari & Soheila Gandomi-Ravandi. (2017) The combined role of heterogeneous catalysis and ultrasonic waves on the facile synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Journal of Saudi Chemical Society 21, pages S415-S424.
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Ágnes Magyar & Zoltán Hell. (2016) One-Pot Three-Component Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones in the Presence of a Molecular Sieve Supported Lanthanum Catalyst. Catalysis Letters 146:6, pages 1153-1162.
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Forugh Havasi, Arash Ghorbani-Choghamarani & Farzad Nikpour. (2016) Synthesis and characterization of nickel complex anchored onto MCM-41 as a novel and reusable nanocatalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Microporous and Mesoporous Materials 224, pages 26-35.
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Roushan Khoshnavazi, Leila Bahrami & Forugh Havasi. (2016) Organic–inorganic hybrid polyoxometalate and its graphene oxide–Fe 3 O 4 nanocomposite, synthesis, characterization and their applications as nanocatalysts for the Knoevenagel condensation and the synthesis of 2,3-dihydroquinazolin-4(1H)-ones . RSC Advances 6:103, pages 100962-100975.
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Nasrin Razavi & Batool Akhlaghinia. (2016) Hydroxyapatite nanoparticles (HAP NPs): a green and efficient heterogeneous catalyst for three-component one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media. New Journal of Chemistry 40:1, pages 447-457.
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Seyedeh Bahareh Azimi & Javad Azizian. (2016) Reaction of benzyl alcohols, isatoic anhydride, and primary amines mediated by I 2 /K 2 CO 3 in water: a new and green approach for the synthesis of 2,3-dihydroquinazolin-4(1 H )-ones. Tetrahedron Letters 57:2, pages 181-184.
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Abolfazl Olyaei, Fatemeh Rahbarian & Mahdieh Sadeghpour. (2015) Green and Catalyst-free One-pot Synthesis Of 2,3-dihydroquinazolin-4(1h)-ones in Water. Chemistry of Heterocyclic Compounds 51:10, pages 899-902.
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Bao-Hua Chen, Ji-Tai Li & Guo-Feng Chen. (2015) Efficient synthesis of 2,3-disubstituted-2,3-dihydroquinazolin-4(1H)-ones catalyzed by dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation. Ultrasonics Sonochemistry 23, pages 59-65.
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S. Nagarajan, Tanveer Mahamadali Shaikh & Elango Kandasamy. (2015) An ionic liquid catalyzed reusable protocol for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one under mild conditions. New Journal of Chemistry 39:12, pages 9693-9699.
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Tao Deng, Hongjun Wang & Chun Cai. (2015) Highly enantioselective synthesis of dihydroquinazolinones through Sc(OTf)3-catalyzed intramolecular amidation of imines. Journal of Fluorine Chemistry 169, pages 72-77.
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Hamid Reza Safaei, Mohsen Shekouhy, Shima Khademi, Vahid Rahmanian & Maryam Safaei. (2014) Diversity-oriented synthesis of quinazoline derivatives using zirconium tetrakis(dodecylsulfate) [Zr(DS)4] as a reusable Lewis acid-surfactant-combined catalyst in tap water. Journal of Industrial and Engineering Chemistry 20:5, pages 3019-3024.
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Sougata Santra, Matiur Rahman, Anupam Roy, Adinath Majee & Alakananda Hajra. (2014) Nano-indium oxide: An efficient catalyst for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones with a greener prospect. Catalysis Communications 49, pages 52-57.
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Parthasaradhi Yerram, Rakhi Chowrasia, Suresh Seeka & Savitha Jyostna Tangenda. (2013) Polyethylene glycol (PEG-400) as a medium for novel and efficient synthesis of 2-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives. European Journal of Chemistry 4:4, pages 462-466.
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Ali A. Mohammadi, Hamed Rohi & Ali Abolhasani Soorki. (2013) Synthesis and In Vitro Antibacterial Activities of Novel 2‐Aryl‐3‐(phenylamino)‐2,3‐dihydroquinazolin‐4(1 H )‐one Derivatives . Journal of Heterocyclic Chemistry 50:5, pages 1129-1133.
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Yijia Chen, Weiguang Shan, Min Lei & Lihong Hu. (2012) Thiamine hydrochloride (VB1) as an efficient promoter for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Tetrahedron Letters 53:44, pages 5923-5925.
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Lijiu Gao, Honglou Ji, Liangce Rong, Dan Tang, Yunyun Zha, Yanhui Shi & Shujiang Tu. (2011) An efficient synthesis of 2,3‐dihydroquinazolin‐4(1 H )‐one derivatives under catalyst‐free and solvent‐free conditions . Journal of Heterocyclic Chemistry 48:4, pages 957-960.
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M. Z. Kassaee, Shahnaz Rostamizadeh, Nasrin Shadjou, Elahe Motamedi & Maryam Esmaeelzadeh. (2010) An efficient one‐pot solvent‐free synthesis of 2,3‐dihydroquinazoline‐4(1H)‐ones via Al/Al 2 O 3 nanoparticles . Journal of Heterocyclic Chemistry 47:6, pages 1421-1424.
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Zhan-Hui Zhang, Hong-Yan Lü, Shu-Hong Yang & Jian-Wu Gao. (2010) Synthesis of 2,3-Dihydroquinazolin-4(1 H )-ones by Three-Component Coupling of Isatoic Anhydride, Amines, and Aldehydes Catalyzed by Magnetic Fe 3 O 4 Nanoparticles in Water . Journal of Combinatorial Chemistry 12:5, pages 643-646.
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A. Davoodnia, S. Allameh, A.R. Fakhari & N. Tavakoli-Hoseini. (2010) Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst. Chinese Chemical Letters 21:5, pages 550-553.
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Shahnaz Rostamizadeh, Hamid Reza Ghaieni, Reza Aryan & Ali Mohammad Amani. (2010) Clean one-pot synthesis of 1,2,4-oxadiazoles under solvent-free conditions using microwave irradiation and potassium fluoride as catalyst and solid support. Tetrahedron 66:2, pages 494-497.
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Shahnaz Rostamizadeh, Ali Mohammad Amani, Reza Aryan, Hamid Reza Ghaieni & Nasrin Shadjou. (2009) ChemInform Abstract: Synthesis of New 2‐Aryl‐Substituted 2,3‐Dihydroquinazoline‐4(1H)‐ones under Solvent‐Free Conditions, Using Molecular Iodine as a Mild and Efficient Catalyst.. ChemInform 40:14.
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Yoshio Kasashima, Atsushi Uzawa, Tadasuke Nishida, Takashi Mino, Masami Sakamoto & Tsutomu Fujita. (2009) Iodine-Catalyzed Synthesis of Five-Membered Cyclic Ethers from 1,3-Diols under Solvent-Free Conditions. Journal of Oleo Science 58:8, pages 421-427.
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