An Expeditious and Green Synthesis of 3,3¢-(Arylmethylene)-bis-(4-hydroxycoumarins) Catalyzed by 5-Sulfosalicylic Acid
Hamzeh Kiyani* and Hassan Darbandi* Author for corresponding; e-mail address: hkiyani@du.ac.ir
Volume: Vol.44 No.3 (July 2017)
Research Article
DOI:
Received: 12 June 2015, Revised: -, Accepted: 4 September 2015, Published: -
Citation: Kiyani H. and Darbandi H., An Expeditious and Green Synthesis of 3,3¢-(Arylmethylene)-bis-(4-hydroxycoumarins) Catalyzed by 5-Sulfosalicylic Acid , Chiang Mai Journal of Science, 2017; 44(3): 1002-1010.
Abstract
The expeditious synthesis of 3,3¢-(arylmethylene)-bis-(4-hydroxycoumarins) via a three-component domino Knoevenagel-Michael reaction (3CDKMR) of various aldehydes and 4-hydroxycoumarin, catalyzed by 5-sulfosalicylic acid (SA) is explored. The reactions were conducted at 80 °C using water as a green and environmentally benign medium. The method has several advantages such as reusability of reaction medium, the avoidance of hazardous organic solvents, readily available reagents, cost-effectiveness, and good to high yields.
Related Articles
DOI: 10.12982/CMJS.2026.011.
Junpeng Liu*, Pan Hu, Hongzhao Gao, Tongtong Wang, Haicheng Jiang, Yiting Wang, Xinyong Liu, Liang Qu, Mianda Huang and Di Fu
Vol.53 No.1 (January 2026)Research Article View: 171 Download: 12
DOI: 10.12982/CMJS.2026.007.
Xiaoyan Su, Yu Zhan and Changhui Li*
Vol.53 No.1 (January 2026)Research Article View: 233 Download: 4
DOI: 10.12982/CMJS.2025.093.
Pengfei Yu and Minquan Feng
Vol.52 No.6 (November 2025)Research Article View: 452 Download: 91
DOI: 10.12982/CMJS.2025.082.
Tzyy Lih Lee, Chun-Chieh Yip, Lloyd Ling, Kok Zee Kwong, Jing-Ying Wong and Foo Wei Lee
Vol.52 No.6 (November 2025)Research Article View: 592 Download: 389
DOI: 10.12982/CMJS.2025.075.
Yan-Min Chen, Zhen-Zhen Chen, Bei-Bei Qi, Ye-Xuan Cai, Jia-Meng Li and Yi-Fan Han
Vol.52 No.5 (September 2025)Research Article View: 1,233 Download: 107
DOI: 10.12982/CMJS.2025.072.
Amin Aadenan, Mohd Norizam Md Daud, Muhammad Aidil Ibrahim, Mohd Hafiz Ahmad and Mohd Asri Mat Teridi
Vol.52 No.5 (September 2025)Research Article View: 754 Download: 109
DOI: 10.12982/CMJS.2025.051.
Maytiya Konkit, Yanika Wacharatewinkul, Wasana Naiumsawang, Wanatchaporn Boontham, Kanya Sornsanit, Kroekkai Janngam, Thongchai Srimuang and Wasu Pathom-aree
Vol.52 No.4 (July 2025)Research Article View: 650 Download: 155
DOI: 10.12982/CMJS.2025.010.
Jirakanit Muttaharach and Wilaiwan Chotigeat
Vol.52 No.1 (January 2025)Research Article View: 832 Download: 243
DOI: 10.12982/CMJS.2024.096.
Ganogwan Sukplang, Chaiyanut Narasettiti, Orawan Chunhachart, Moltira Srithaworn, Wanlapa Lorliam, Sukhumaporn Krajangsang and Titiporn Panyachanakul
Vol.51 No.6 (November 2024)Research Article View: 999 Download: 1,032
DOI: 10.12982/CMJS.2024.095.
Zhen Liu, Yiwei Fu, Jiangsong Jiang, Ya Huang, Dong Li, Yikun Yue, Shaochun Yuan and Chengzhi Wang
Vol.51 No.6 (November 2024)Research Article View: 1,037 Download: 509
DOI: 10.12982/CMJS.2024.092.
Hieu Van Nguyen, Cuong Van Duong, Nattawut Sareein, Christine Jewel C. Uy-Yabut, Anh Duc Tran and Vinh Van Nguyen
Vol.51 No.6 (November 2024)Research Article View: 1,044 Download: 538
DOI: 10.12982/CMJS.2024.074.
Aumaparn Phlayrahan and Sirintra Boonchu
Vol.51 No.5 (September 2024)Research Article View: 1,305 Download: 537
DOI: 10.12982/CMJS.2024.067.
Md. Enamul Huq, David Lopez-Carr, Fahad Almutlaq, Xijun Wu and Jiang Wu
Vol.51 No.5 (September 2024)Research Article View: 1,636 Download: 452
DOI: 10.12982/CMJS.2024.055.
Kamonlak Chailangka, Rawisara Ruenwai, Trakul Prommajak and Ratana Attabhanyo
Vol.51 No.4 (July 2024)Research Article View: 1,599 Download: 1,779
DOI: 10.12982/CMJS.2024.053.
Lijuan Zhang, Jian Ma, Tianming Zhao, Meiyan Han, Dege Zheng, Ruvishika S. Jayawardena, Ausana Mapook and Yongzhong Lu
Vol.51 No.4 (July 2024)Research Article View: 1,740 Download: 715
DOI: 10.12982/CMJS.2024.026.
Mohd Amirul Mukmin Abdullah, Nur Aisyah Shafie, Mazrul Nizam Abu Seman and Syamsul B. Abdullah
Vol.51 No.2 (March 2024)Research Article View: 1,494 Download: 729
DOI: 10.12982/CMJS.2024.010.
Parnuch Hongsawat, Phuri Kalnaowakul and Panida Prarat
Vol.51 No.1 (January 2024)Research Article View: 1,691 Download: 624
DOI: 10.12982/CMJS.2024.008.
Chanin Kaewmanee, Chotiwut Techakijvej and Chitchol Phalaraksh
Vol.51 No.1 (January 2024)Research Article View: 2,195 Download: 777
DOI: 10.12982/CMJS.2023.057.
Kritchanon Suanjan, Warunsak Liamlaem, Nutta Sangnarin Hamjinda and Chongrak Polprasert
Vol.50 No.6 (November 2023)Research Article View: 959 Download: 573
DOI: 10.12982/CMJS.2022.107.
Chattarika Sukpattanacharoen, Wasin Somboot, Jaroon Jakmunee and Tinakorn Kanyanee
Vol.49 No.6 (November 2022)Research Article View: 1,434 Download: 580
DOI: 10.12982/CMJS.2022.096.
Montree Sangthongdee, Supanut Phattarateera and Poonsub Threepopnatkul
Vol.49 No.6 (November 2022)Research Article View: 1,137 Download: 792
DOI: 10.12982/CMJS.2022.093.
Anan O-Manee, Youichi Enokida and Kayo Sawada
Vol.49 No.5 (September 2022)Research Article View: 1,663 Download: 637
DOI: 10.12982/CMJS.2022.048.
Sheng Xu, Rungtiwa Phookamsak, Hong-Bo Jiang, Saowaluck Tibpromma, Jian-Bo Yang, Jian-Chu Xu and Saisamorn Lumyong
Vol.49 No.3 (Special Issue II : May 2022)Research Article View: 1,722 Download: 428
DOI: 10.12982/CMJS.2022.060.
Tanawan Sukkasem, Uraiwan Tippayasak, Pornchanok Taweecheep, Duenrut Chonudomkul and Gunjana Theeragool
Vol.49 No.4 (July 2022)Research Article View: 1,849 Download: 544
DOI: 10.12982/CMJS.2022.043.
Jessica Gina Lomonaco, Opas Tojira, Sumittra Charojrochkul and Pannipa Tepamatr
Vol.49 No.4 (July 2022)Research Article View: 1,972 Download: 1,004
page: 1511 - 1523
Kamonwat Nakason, Pongtanawat Khemthong, Wasawat Kraithong, Suwisa Mahasandana and Bunyarit Panyapinyopol
Vol.48 No.6 (November 2021)Research Article View: 1,722 Download: 726
page: 1036 - 1044
Jinfeng Yang, Myong Jo Kim, Weiling Chen, Yong Soo Kwon and Ji Hye Yoo
Vol.48 No.4 (July 2021)Research Article View: 1,219 Download: 129
page: 1057 - 1067
Chandrasekaran Ramprasad and Busetty Subramanayam
Vol.48 No.4 (July 2021)Research Article View: 1,003 Download: 500
page: -
Editorial Board
Vol.48 No.3 (Special Issue I : May 2021)Content View: 1,090 Download: 487
page: 533 - 544
Supamas Danwittayakul* and Phutthamon Chantes
Vol.48 No.2 (March 2021)Research Article View: 961 Download: 458
page: 301 - 311
Wisan Chananchana, Jaroon Junsomboon, Manuel Miró and Jaroon Jakmunee*
Vol.48 No.2 (March 2021)Research Article View: 1,690 Download: 609
page: 74 - 89
Prapaparn Sirikhansaeng, Niphaphat Phukoetphim, Pattana Laopaiboon and Lakkana Laopaiboon*
Vol.48 No.1 (January 2021)Research Article View: 1,430 Download: 655
page: 1055 - 1067
Wei Zhao, Youning Chen and Yuhong Li
Vol.47 No.5 (September 2020)Research Article View: 1,476 Download: 419
page: 28 - 38
Hyesung Park, Pradeep Puligundla and Chulkyoon Mok*
Vol.47 No.1 (January 2020)Research Article View: 1,187 Download: 799
page: 1129 - 1142
Manuswee Phanichnok, Khanidtha Meevasana and Pongthep Suwanwaree*
Vol.46 No.6 (November 2019)Research Article View: 1,276 Download: 1,217
page: 255 - 259
Niwooti Whangchai*, Nakao Nomura and Masatoshi Matsumura
Vol.30 No.3 (DECEMBER 2003)Research Article View: 891 Download: 259
page: 85 - 94
Yuwadee Peerapornpisal*, Chomyong Chaiubol, Jeeraporn Pekkoh, Hathaitip Kraibut, Manida Chorum, Pittsanu Wannathong, Neti Ngearnpat, Kajeewan Jusakul, Angkhana Thammathiwat, Janchira Chuanunta and Thanisara Inthasotti
Vol.31 No.1 (JANUARY 2004)Research Article View: 1,873 Download: 460
page: 69 - 84
Tossapon Vijaranakorn, Pamornwan Nutniyom and Somporn Chantara*
Vol.31 No.1 (JANUARY 2004)Research Article View: 1,159 Download: 275
page: 247 - 253
Alissara Reungsang* and Suksamarn Sangyoka
Vol.30 No.3 (DECEMBER 2003)Research Article View: 966 Download: 255
page: 227 - 233
Sukru Asian and Aysen Turkman
Vol.30 No.3 (DECEMBER 2003)Research Article View: 893 Download: 248
page: 219 - 226
Wimal A.H.P.Guruge, Nallahandhi J. De S. Amarasinghe, Pallage M.C.S De Silva and Colamba H. Priyantha
Vol.30 No.3 (DECEMBER 2003)Research Article View: 1,015 Download: 258
page: 211 - 217
Jeeraporn Pekkoh*, Yuwadee Peerapornpisal, Suwiwek Lipigorngoson and Sakorn Promkutkaew
Vol.30 No.3 (DECEMBER 2003)Research Article View: 1,246 Download: 305
page: 203 - 209
Rattapoom Prommana*, Yuwadee Peerapornpisal, Suwiwek Lipigorngoson and Sakorn Promkulkaew
Vol.30 No.3 (DECEMBER 2003)Research Article View: 1,085 Download: 386
page: 195 - 202
Suparb Paramee*, Amnat Chidthaisong, Sirintornthep Towprayoon, Nipon Tangtham, Pongpor Asnachinda and Viadimir N. Bashkin
Vol.30 No.3 (DECEMBER 2003)Research Article View: 957 Download: 462
page: 189 - 193
Tatporn Kunpradid* and Yuwadee Peerapornpisal
Vol.30 No.3 (DECEMBER 2003)Research Article View: 1,140 Download: 616
page: 175 - 187
Geoffrey A. Codd, Louise F. Morrison and James S. Metcalf
Vol.30 No.3 (DECEMBER 2003)Research Article View: 1,097 Download: 288
page: 165 - 173
Chongrak Polprasert* and Kusumakar Sharma
Vol.30 No.3 (DECEMBER 2003)Research Article View: 913 Download: 261
page: 141 - 152
Visith Chavasit, Ornsurang Teerawat, Yutana Norapoompipat and Tipvon Parinyasiri
Vol.30 No.3 (DECEMBER 2003)Research Article View: 1,041 Download: 205
page: 353 - 360
Vicit Rizal Eh Suk*, Khalisanni Khalid and Misni Misran
Vol.46 No.2 (March 2019)Research Article View: 1,123 Download: 1,171
page: 2211 - 2219
Sunisa Jindasuwan, Mantana Suwan and Sitthisuntorn Supothina
Vol.45 No.5 (Special 2018)Research Article View: 982 Download: 405
page: 2190 - 2194
Nutthita Chuankrerkkul, Thanakorn Wasanapiarnpong and Khanittha Noomun
Vol.45 No.5 (Special 2018)Research Article View: 991 Download: 322
page: 1460 - 1470
Musa Buyukada*, Mirac Eryigit and Fatih Evrendilek
Vol.45 No.3 (May 2018)Research Article View: 1,676 Download: 290
page: 1318 - 1322
Niwooti Whangchai*, Chanagun Chitmanat, Rameshprabu Ramaraj and Tomoaki Itayama
Vol.45 No.3 (May 2018)Research Article View: 1,302 Download: 496
page: 1015 - 1029
Erasto Mlyuka, Martha Mbifile, Shuang Zhang, Zongping Zheng and Jie Chen*
Vol.45 No.2 (March 2018)Research Article View: 1,019 Download: 629
page: 188 - 197
Natthawud Dussadee, Rameshprabu Ramaraj and Nyanakorn Sutassanamarlee
Vol.45 No.1 (January 2018)Research Article View: 948 Download: 423
page: 1654 - 1668
Tongchai Sriwiriyarat*, Rapeepan Wongvian and Sinchai Kuhakaew
Vol.44 No.4 (October 2017)Research Article View: 932 Download: 501
page: 1534 - 1547
Erasto Mlyuka, Shuang Zhang, Zongping Zheng, Zhiyong He, Maomao Zeng, Martha Mbifile and Jie Chen*
Vol.44 No.4 (October 2017)Research Article View: 1,046 Download: 391
page: 1356 - 1366
Songyot Kullasoot, Piyamas Intrarasattayapong and Chitchol Phalaraksh*
Vol.44 No.4 (October 2017)Research Article View: 1,596 Download: 497
page: 1040 - 1048
Javaid Akhtar, NorAishah Saidina Amin* and Muhammad Usman Rashid
Vol.44 No.3 (July 2017)Research Article View: 950 Download: 207
page: 1011 - 1021
Hamzeh Kiyani* and Heshmat Allah Samimi
Vol.44 No.3 (July 2017)Research Article View: 1,060 Download: 330
page: 988 - 992
Pramote Khuwijitjaru*, Intira Koomyart, Takashi Kobayashi and Shuji Adachi
Vol.44 No.3 (July 2017)Research Article View: 1,132 Download: 544
page: 731 - 741
Chariya Chomvarin*, Warawan Wongboot, Aschana Tirapattanun, Sakawrat Kanthawong, Suwin Wongwajana,
Vol.44 No.3 (July 2017)Research Article View: 929 Download: 527
page: 309 - 321
Onanong Pringsulaka* [a], Nuttika Suwannasai [a], Sirinthorn Sunthornthummas [b], Sukhumaporn Krajan
Vol.44 No.2 (April 2017)Research Article View: 946 Download: 702
page: 1335 - 1345
Dony Adriansyah Nazaruddin*, ZafirahSakinah Amiruzan, Hamzah Hussin, Mohammad Muqtada Ali Khan,...
Vol.43 No.6 (SPECIAL ISSUE 2)Research Article View: 928 Download: 464
page: 1048 - 1058
Theerasak Somdee* [a], Anchana Somdee [a], John Ruck [b], Margaret Allison [b] and Rachel Page [b]
Vol.43 No.5 (OCTOBER 2016)Research Article View: 883 Download: 830
page: 1037 - 1047
Pamon Pumas* [a] and Chayakorn Pumas [b,c]
Vol.43 No.5 (OCTOBER 2016)Research Article View: 954 Download: 430
page: 375 - 380
Nutthita Chuankrerkkul*[a], Kritkaew Somton [b], Thassanee Wonglom [b], Kannigar Dateraksa [b] and P
Vol.43 No.2 (SPECIAL ISSUE 1)Research Article View: 902 Download: 395
page: 1044 - 1053
Manad Khamkong*[a] and Putipong Bookkamana[a]
Vol.42 No.4 (OCTOBER 2015)Research Article View: 1,075 Download: 321
page: 560 - 577
Sirikhae Pongswat and Sutthawan Suphan
Vol.42 No.3 (JULY 2015)Research Article View: 888 Download: 314
page: 549 - 559
Rameshprabu Ramaraj, David Da-Wei Tsai and Paris Honglay Chen
Vol.42 No.3 (JULY 2015)Research Article View: 966 Download: 286
page: 436 - 442
Thammasit Vongsetskul, Thanaphorn Chantarodsakun, Preeyaphorn Wongsomboon, Ratth Rangk
Vol.42 No.2 (APRIL 2015)Research Article View: 1,068 Download: 326
page: 417 - 428
Shahram. Nekouei, Farzin.Nekouei
Vol.42 No.2 (APRIL 2015)Research Article View: 926 Download: 317
page: 1065 - 1076
Tippawan Prasertsin, Jeeraporn Pekkoh, Wasu Pathom- aree and Yuwadee Peerapornpisal*
Vol.41 No.5/1 (OCTOBER 2014)Research Article View: 864 Download: 197
page: 1195 - 1207
Pimporn Leelapornpisid, Lapatrada Mungmai, Busabun Sirithunyalug, Supat Jiranusornkul and Yuwadee Peerapornpisal
Vol.41 No.5/2 (OCTOBER 2014)Research Article View: 1,014 Download: 414
page: 344 - 355
Amphorn Sakset* [a] and Wanninee Chankaew* [b]
Vol.40 No.3 (JULY 2013)Research Article View: 999 Download: 628
page: 294 - 298
Suteera Srisamai, Phonlawat Srikhampa, and Wasu Pathom-aree*
Vol.40 No.2 (APRIL 2013)Research Article View: 1,374 Download: 273
page: 410 - 428
Chompunut Chayawat*[a], Chuckree Senthong[a], Monique Y.Leclerc[b], Gengsheng Zhang[b] and John P. B
Vol.39 No.3 (JULY 2012)Research Article View: 823 Download: 299
page: 292 - 299
Walailuck Boonchum[a], Panmuk Vacharapiyasophon[a], Duangta Kanjanapothi[b], Jeeraporn Pekkoh[a], Do
Vol.39 No.2 (APRIL 2012)Research Article View: 892 Download: 285
page: 280 - 294
Pongpan Leelahakriengkrai*[a] and Yuwadee Peerapornpisal [a,b]
Vol.38 No.2 (APRIL 2011)Research Article View: 964 Download: 472
page: 223 - 230
Voranuch Somsongkul [a], Chaiyuth Saekung [b], San H. Thang [c], Atchana Wongchaisuwat [a] and Mari
Vol.38 No.2 (APRIL 2011)Research Article View: 988 Download: 260
page: 126 - 138
Aranya Manosroi, Walailak Witkittilak, Romchat Chutoprapat, Hiroaki Todo, Kenji Sugibayashi, Worapak
Vol.38 No.1 (JANUARY 2011)Research Article View: 887 Download: 256
page: 89 - 96
Niwooti Whangchai, Thepparath Ungsethaphand, Chanagun Chitmanat, Kriangsak Mengumphan and Supattra
Vol.34 No.1 (JANUARY 2007)Research Article View: 921 Download: 427
page: 73 - 78
Terdsak Subtavewung, and Fongsaward S. Singharajwarapan
Vol.34 No.1 (JANUARY 2007)Research Article View: 923 Download: 768
page: 253 - 268
Khajornkiat Saeton, and Siripen Traichaiyaporn
Vol.34 No.2 (MAY 2007)Research Article View: 929 Download: 268
page: 212 - 220
Chinnavat Thawornkuno and Chanin Panjapornpon
Vol.35 No.1 (JANUARY 2008)Research Article View: 977 Download: 978
page: 123 - 130
Parichat Budrat and Artiwan Shotipruk
Vol.35 No.1 (JANUARY 2008)Research Article View: 1,091 Download: 677
page: 116 - 122
Wasinee Kaewboonnum, Ketmanee Wachararuji and Artiwan Shotipruk
Vol.35 No.1 (JANUARY 2008)Research Article View: 1,050 Download: 262
page: 103 - 108
Rangsriwong P., Rangkadilok N., and Shotipruk A
Vol.35 No.1 (JANUARY 2008)Research Article View: 975 Download: 267
page: 69 - 81
Woranart Jonglertjunya
Vol.35 No.1 (JANUARY 2008)Research Article View: 975 Download: 294
page: 224 - 235
Kim Jenkins, Richard Kingsford, and Darren Ryder
Vol.36 No.2 (MAY 2009)Short Communication View: 940 Download: 375
page: 149 - 157
Suwasa Kantawanichkul, Seni Karnchanawong, and Shuh Ren Jing
Vol.36 No.2 (MAY 2009)Short Communication View: 1,060 Download: 304
page: 369 - 383
Jaroon Junsomboon, Ponlayuth Sooksamiti, Kate Grudpan, Somchai Lapanantnoppakhun, Prasak Thavornyuth
Vol.36 No.3 (SEPTEMBER 2009)Research Article View: 977 Download: 248
page: 151 - 159
Somyot Silalom, James L. Carter, and Porntip Chantaramongkol
Vol.37 No.1 (JANUARY 2010)Research Article View: 957 Download: 249
page: 74 - 84
Emmanuel U. Onweremadu, Ogochukwu P. Izuogu, and Frank O.R. Akamigbo
Vol.37 No.1 (JANUARY 2010)Research Article View: 996 Download: 307
page: 7 - 13
Abu Sayed Md. Kamal* and Preeda Parkpian
Vol.29 No.1 (APRIL 2002)Research Article View: 952 Download: 313
page: 97 - 112
Trai Pekthong and Yuwadee Peerapornpisal
Vol.28 No.2 (DECEMBER 2001)Opinion View: 913 Download: 282
page: 9 - 15
Wanna Kanchanamayoon, Sirichai Hathongkam and Amnat Laothong
Vol.28 No.1 (JUNE 2001)Opinion View: 948 Download: 508
page: 102 - 113
Weerasak Roongruangwongse [a], Pongpor Asnachinda [b] and Wanchai Sonthichai [a]
Vol.27 No.2 (DECEMBER 2000)Opinion View: 1,088 Download: 265
page: 344 - 354
Mohammed A.A. Khan, Zaini B. Assim, and Norhadi Ismail
Vol.37 No.2 (MAY 2010)Research Article View: 971 Download: 397