Co-reporter:Jinming Fan, Tao Wang, Chenchen Li, Rui Wang, Xiaoyu Lei, Yong Liang, and Zunting Zhang
Organic Letters November 3, 2017 Volume 19(Issue 21) pp:5984-5984
Publication Date(Web):October 19, 2017
DOI:10.1021/acs.orglett.7b03007
A concise and efficient photoinduced rearrangement of (E)-3-arylvinyl-4H-chromen-4-ones for the synthesis of benzoaryl-5-yl(2-hydroxyphenyl)methanones is described. Benzoaryl-5-yl-(2-hydroxyphenyl)methanones were obtained in 77–95% yields via the irradiation of (E)-3-arylvinyl-chromones in the 95% EtOH with a high-pressure mercury lamp at room temperature under Ar atmosphere. The reported method provides a novel procedure for the synthesis of α,α′-diaryl ketone derivatives without addition of any transition metals and oxidants or other additives. A plausible mechanism was proposed, and the rearrangement product was characterized by NMR, HRMS, and X-ray.
Co-reporter:Jie Han, Tao Wang, Yong Liang, Ying Li, Chenchen Li, Rui Wang, Siqi Feng, and Zunting Zhang
Organic Letters July 7, 2017 Volume 19(Issue 13) pp:
Publication Date(Web):June 15, 2017
DOI:10.1021/acs.orglett.7b01531
An efficient transition-metal-free photoinduced intracyclization of 4H-chromen-4-ones in EtOH–H2O (7:1, v/v) at ambient temperature for the construction of complicated fused-ring heteroaromatics is established. The reaction proceeds smoothly without requiring any catalysts/additives.
Co-reporter:Jin Zhang, Xi Zhang, Tao Wang, Xinbo Yao, Pei Wang, Ping Wang, Sisi Jing, Yong Liang, and Zunting Zhang
The Journal of Organic Chemistry December 1, 2017 Volume 82(Issue 23) pp:12097-12097
Publication Date(Web):October 24, 2017
DOI:10.1021/acs.joc.7b01839
A photoinduced direct oxidative annulation of 1-aryl-2-(furan/thiophen-2-yl)butane-1,3-diones and ethyl-2-(furan-2-yl)-3-oxo-3-(aryl-2-yl)propanoates in EtOH without the need for any transition metals and oxidants provided access to highly functionalized polyheterocyclic 1-(5-hydroxynaphtho[2,1-b]furan-4-yl)ethanones and 1-(5-hydroxyfuran/thieno/pyrrolo[3,2-e]benzofuran-4-yl)ethanones. The phenomenon of excited-state intramolecular proton transfer (ESIPT) was observed for both 1-(5-hydroxynaphtho[2,1-b]furan-4-yl)ethanone and 1-(5-hydroxy furan/thieno/pyrrolo[3,2-e]benzofuran-4-yl)ethanone analogues.
Co-reporter:Jin Zhang;Ju-Fang Peng;Tao Wang;Yang Kang;Sisi Jing
Molecular Diversity 2017 Volume 21( Issue 2) pp:317-323
Publication Date(Web):28 February 2017
DOI:10.1007/s11030-017-9727-x
3-phenol-1H-pyrazoles (2), 4-halogeno-3-phenol-1H-pyrazoles (3) and 2-(1-phenol-1H-pyrazol-5-yl)phenols (4) were prepared by the condensation of (E)-3-(dimethylamino)-1-phenylprop-2-en-1-ones and hydrazine hydrate or phenylhydrazine in good yields. They were evaluated against five phytopathogens fungi, namely Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani and Fusarium solani in vitro. Most of the above-mentioned compounds exhibited activities. For example, 4-chloro-2-(1H-pyrazol-3-yl)phenol (3k) and 4-bromo-3-phenol-1H-pyrazole (3b) showed good and broad-spectrum antifungal properties against Cytospora sp., C. gloeosporioides, Botrytis cinerea, Alternaria solani and F. Solani with \(\hbox {IC}_{50}\) values ranging from 4.66 to 12.47 \(\upmu \)g/mL. The results showed that pyrazoles with one aryl group at 3-position (2 and 3) exhibited better antibacterial activity than those with two aryl substituents (4). In addition, the existence of an electron-withdrawing group, a substituent on the ortho-position of phenol ring or a halogen atom at the 4-position of the pyrazole enhanced the antifungal activity of pyrazoles 2 and 3.
Co-reporter:Qian Yang;Yun He;Tao Wang;Lingyu Zeng;Zunting Zhang
Molecular Diversity 2016 Volume 20( Issue 1) pp:9-16
Publication Date(Web):2016 February
DOI:10.1007/s11030-015-9620-4
The direct coupling of 3-iodochromen-4-ones with heteroaromatics has been achieved via a photochemical reaction. A variety of 3-heteroarylchromones was obtained in moderate to good yields from the corresponding 3-iodochromen-4-ones and heteroaromatics, such as pyrrole, furan, thiophene, and benzofuran. The reaction worked smoothly in acetonitrile under a mercury lamp without any additives, providing a catalyst- and base-free approach for the synthesis of 3-heteroarylchromones.
Co-reporter:Jin Zhang;Ju-Fang Peng;Yu-Bin Bai;Ping Wang;Tao Wang
Molecular Diversity 2016 Volume 20( Issue 4) pp:887-896
Publication Date(Web):2016 November
DOI:10.1007/s11030-016-9690-y
5,6-Diarylpyrazolo[1,5-a]pyrimidines (3) and 6,7-diarylpyrazolo[1,5-a]pyrimidines (4) were chemoselectively synthesized by the condensation of isoflavone (1) and 3-aminopyrazole (2). 5,6-Diarylpyrazolo[1,5-a]pyrimidines (3) were obtained via microwave irradiation, and 6,7-diarylpyrazolo[1,5-a]pyrimidines (4) were obtained via conventional heating. In addition, the pyrimidine derivatives 3 and 4 were evaluated against five phytopathogenic fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani) using the mycelium growth rate method. Some of them were effective in inhibiting the growth of the five phytopathogenic fungi. For instance, 6,7-diarylpyrazolo[1,5-a]pyrimidines (4j) inhibited the growth of A. solani with an \(\hbox {IC}_{50}\) value of 17.11 \(\upmu \hbox {g}/\hbox {mL}\), and 6,7-diarylpyrazolo[1,5-a]pyrimidines (4h) inhibited the growth of both Cytospora sp. and F. solani with \(\hbox {IC}_{50}\) values of 27.32 and 21.04 \(\upmu \hbox {g}/\hbox {mL}\), respectively.
Co-reporter:Qing He, Liwen Wang, Yong Liang, Zunting Zhang, and Stanislaw F. Wnuk
The Journal of Organic Chemistry 2016 Volume 81(Issue 19) pp:9422-9427
Publication Date(Web):August 29, 2016
DOI:10.1021/acs.joc.6b01648
Transition-metal-free LiCl-promoted cross-coupling reactions of tetraphenyltin, trichlorophenyl-, dichlorodiphenyl-, and chlorotriphenylstannanes with aryl halides in DMF provided access to biaryls in good to high yields. Up to four phenyl groups were transferred from the organostannanes substrates. The aryls bearing electron-withdrawing groups in either halides or organotin substrates gave coupling products in higher yields. The methodology has been applied for the efficient synthesis of ipriflavones.
Co-reporter:Qian Yang;Tao Wei;Yun He;Yong Liang
Helvetica Chimica Acta 2015 Volume 98( Issue 7) pp:953-960
Publication Date(Web):
DOI:10.1002/hlca.201400351
Abstract
A method for the direct arylation of 5-iodouracil and 5-iodouridine was found to proceed in moderate yields. By irradiating mixtures of 5-iodouracil or 5-iodouridine and a series of five-membered heterocycles such as 1H-pyrrole, furan, 2-methylfuran, 1-methyl-1H-pyrrole, thiophene, as well as benzene in MeCN/H2O with a Hg lamp, 5-aryluracils and 5-aryluridines were synthesized. The reaction proceeded smoothly without the requirement of adding any transition metals or ligands.
Co-reporter:Qian Yang;Zunting Zhang;Bo Liang
Journal of Heterocyclic Chemistry 2015 Volume 52( Issue 1) pp:310-316
Publication Date(Web):
DOI:10.1002/jhet.2035
A new concise, facile, and efficient method for synthesis of 3-thiophenchromone was accomplished in more than over 80% yield starting from formation of the substituted 3-iodochromones and tetrathiophentins by Stille cross-coupling reaction in the presence of palladium on charcoal-catalyzed ligand-free under mild conditions.
Co-reporter:Junling Yang;Zunting Zhang ;Qing He
Journal of Heterocyclic Chemistry 2014 Volume 51( Issue 1) pp:24-29
Publication Date(Web):
DOI:10.1002/jhet.1633
Co-reporter:Juanjuan Wang, Zunting Zhang, Wenli Wang and Fangfang Liu
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 12) pp:2034-2038
Publication Date(Web):22 Jan 2013
DOI:10.1039/C3OB27247H
The one-step cyclocondensation of substituted isoflavones with cyanothioacetamide in the presence of sodium hydroxide gave an array of 3-cyano-5,6-diaryl pyridine-2(1H)-thiones in good yields. The procedure involves base-mediated ring opening of the isoflavones and subsequent Knoevenagel condensation between the 1,3-dicarbonyl intermediate generated from the isoflavones and cyanothioacetamide, followed by ring closure and dehydration.
Co-reporter:Zun-Ting Zhang, Qiu-Ya Wang, Wu-Wu Li, Qing-Hua Meng and Xue-Ling Zhang
CrystEngComm 2012 vol. 14(Issue 15) pp:5042-5052
Publication Date(Web):12 Jun 2012
DOI:10.1039/C2CE25173F
Four novel 3D metal–organic frameworks, [Ba (H2O)4 (L1)2]·4H2O (1), [Ba(H2O)4(L2)2]·8H2O (2) [Ba(H2O)7](L3)2·2H2O (3) and [Ba(H2O)7(L4)2]·3H2O (4) were obtained by self-assembly of barium(II) with four isoflavonesulfonate ligands [L1 = 7,4′-dihydroxyisoflavone-3′-sulfonate, L2 = 4′- hydroxy-7-methoxyisoflavone-3′-sulfonate, L3 = 5-hydroxy-7,4′-dimethoxyisoflavone-3′-sulfonate, L4 = 5,7-dihydroxy-6,4′-dimethoxyisoflavone-3′-sulfonate]. To survey the influences of different substituents in isoflavonesulfonate ligands on their self-assembly manners, the crystal structures of 1–4 have been determined by single-crystal X-ray diffraction. The results show that they have an intriguing variety of coordination modes and stacking manners with the changes of substituents in isoflavonesulfonate ligands. The sulfo-groups of isoflavonesulfonate ligands play important roles, they not only can coordinate with Ba2+ directly, but also provide an important bridge in a structural link between the hydrophilic region and the hydrophobic region in the crystal structure of 1–4.
Co-reporter:Zunting Zhang;Pengfei Zhang;Taoying Kang;Mulin Zhu
Chinese Journal of Chemistry 2012 Volume 30( Issue 4) pp:997-1000
Publication Date(Web):
DOI:10.1002/cjoc.201100405
Abstract
Microwave irradiation was used to accelerate the cyclocondensation of isoflavones and 5-amino-1H-imidazole-4-carboxamide in the presence of sodium hydroxide to produce 3,4-diphenyl-imidazo[1,5-a]pyrimidines in good to moderate yields.
Co-reporter:Gang Li;Li-Yan Dai;Yin-Li Du ;Dong Xue
Helvetica Chimica Acta 2012 Volume 95( Issue 6) pp:989-997
Publication Date(Web):
DOI:10.1002/hlca.201100495
Abstract
A series of novel 6-[(1,3,4-thiadiazol-2-yl)sulfanyl]-7-phenylpyrazolo[1,5-a]pyrimidines, 5-phenyl-6-[(1,3,4-thiadiazol-2-yl)sulfanyl]imidazo[1,2-a]pyrimidines, and 2-phenyl-3-[(1,3,4-thiadiazol-2-yl)sulfanyl]pyrimido[1,2-a]benzimidazoles have been synthesized in four steps starting with 2-hydroxyacetophenone. The intermediate 3-[(1,3,4-thiadiazol-2-yl)sulfanyl]-4H-1-benzopyran-4-ones reacted with pyrazol-3-amines, 5-methylpyrazol-3-amine, and 1H-imidazol-2-amine, 1H-benzimidazol-2-amine via a cyclocondensation to give the title compounds in the presence of MeONa as base, respectively. The approach affords the target compounds in acceptable-to-good yields. The new compounds were characterized by their IR, NMR, and HR mass spectra.
Co-reporter:Zun-Ting Zhang;Yu-Qing Ma;Yong Liang;Dong Xue ;Qing He
Journal of Heterocyclic Chemistry 2011 Volume 48( Issue 2) pp:279-285
Publication Date(Web):
DOI:10.1002/jhet.546
Abstract
Direct synthetic methods of 6,7-diphenylpyrazolo[1,5-a]pyrimidine derivatives have been developed. Cyclocondensation of isoflavones with 3-aminopyrazole in the presence of sodium methoxide as alkali promoter gave 6,7-diphenylpyrazolo[1,5-a]pyrimidines in moderate to good yields. J. Heterocyclic Chem., (2011).
Co-reporter:Chuang-Jun Zhang;Wen-Yong Han;Mi-Xiang Gao;Fei-Fei Xu
Journal of Heterocyclic Chemistry 2011 Volume 48( Issue 5) pp:1073-1078
Publication Date(Web):
DOI:10.1002/jhet.606
Abstract
A simple and straightforward methodology towards the synthesis of 2,4,5-trisubstituted pyrimidines has been developed by one-step reaction of isoflavones with thiourea or guanidine. Ten 2-mercapto-4,5-diphenylpyrimidines and eight 2-amino-4,5-diphenylpyrimidines were reported. All of them were characterized by FT-IR, NMR, and elemental analysis. A variety of substrates can participate in the process with good yields and high purities, making this methodology suitable for library synthesis in drug discovery. J. Heterocyclic Chem., (2011).
Co-reporter:Zun-Ting Zhang, Yong Liang, Yu-Qing Ma, Dong Xue and Jun-Ling Yang
ACS Combinatorial Science 2010 Volume 12(Issue 4) pp:600
Publication Date(Web):June 4, 2010
DOI:10.1021/cc1000506
A new concise, facile, and efficient method for the synthesis of 3-hydroxy-5,6-diphenylpyrazolo[3,4-b]pyridine derivatives has been described. The cyclocondensation of isoflavones with 3-amino-5-hydroxypyrazole in the presence of sodium methoxide gave fused heteroaromatic 3-hydroxy-5,6-diphenylpyrazolo[3,4-b]pyridines in moderate to good yields.
Co-reporter:Zun-Ting Zhang, Li Qiu, Dong Xue, Jing Wu and Fei-Fei Xu
ACS Combinatorial Science 2010 Volume 12(Issue 2) pp:225
Publication Date(Web):December 30, 2009
DOI:10.1021/cc900064q
The 2,3-diarylpyrimido[1,2-a]benzimidazole derivatives were prepared by one-step cyclocondensation of 2-aminobenzimidazole with isoflavone in methanol. Single-crystal diffraction analysis was performed for 2-(2-hydroxyl-4-isopropoxy-phenyl)-3-phenylpyrimido[1,2-a]benzimidazole. The fluorescence properties of the fused 2, 3-diarylpyrimido[1, 2-a]benzimidazole were evaluated.
Co-reporter:Wen-Yong Han;Ying-Chun Zhang;Dong Xue;Gang Li
Helvetica Chimica Acta 2010 Volume 93( Issue 8) pp:1641-1649
Publication Date(Web):
DOI:10.1002/hlca.200900438
Abstract
A simple and straightforward methodology toward the synthesis of novel 1-(4,5-diphenylpyrimidin-2-yl)thiourea has been developed by a one-step reaction of isoflavones with amidinothiourea. A series of 16 new compounds was synthesized. All compounds were characterized by FT-IR, NMR, and elemental analysis. The structure of a typical compound was established by X-ray diffraction. A variety of substrates can participate in the process with good yields and high purities, making this methodology suitable for library synthesis in drug discovery.
Co-reporter:Zun-Ting Zhang;Wen-Yong Han ;Li Qiu
Journal of Heterocyclic Chemistry 2010 Volume 47( Issue 5) pp:1209-1214
Publication Date(Web):
DOI:10.1002/jhet.466
Co-reporter:Zun-Ting Zhang;Mi-Xiang Gao;Qing He
Journal of Chemical Crystallography 2010 Volume 40( Issue 10) pp:841-845
Publication Date(Web):2010 October
DOI:10.1007/s10870-010-9751-5
2-Amino-7,4′-dimethoxyisoflavone (I), C17H15NO4 and 2-amino-7-methoxy-4′-hydroxyisoflavone (II), C16H13NO4 were synthesized and their crystal structures were determined by single-crystal X-ray diffraction. They all crystallize in the monoclinic crystal system, space group P21/c. The cell dimensions of I are a = 15.6673(17) Å, b = 7.3998(8) Å, c = 13.2919(14) Å, β = 111.4460(10)°, Dc = 1.377 mg/mm3, V = 1,434.3(3) A3, Z = 4 and those of II are a = 10.990(7) Å, b = 11.879(7) Å, c = 10.422(6) Å, β = 96.904(11)°, Dc = 1.393 mg/mm3, V = 1,350.8(14) A3, Z = 4. A combination of F-type and T-type aromatic–aromatic interaction and hydrogen bonding links the molecules of I into a tri-dimensional framework structure. In the crystal structure of II, paired tri-centered hydrogen bond generates a R42(21) ring and the R42(21) rings link the molecules into a sheet.
Co-reporter:Zun-Ting Zhang, Fei-Fei Xu, Mi-Xiang Gao and Li Qiu
ACS Combinatorial Science 2009 Volume 11(Issue 5) pp:880
Publication Date(Web):July 21, 2009
DOI:10.1021/cc900058y
A simple and straightforward methodology toward the synthesis of novel 4,5-biphenyl-2-pyrimidinylguanidine compounds has been developed by one-pot reaction of biguaninde or dimethyldiguanide with isoflavones. A series of 20 new compounds was reported. All of them were characterized by FT-IR, NMR, and elemental analysis. A typical compound was determined by X-ray diffraction. A variety of substrates can participate in the process with good yields and high purities, making this methodology suitable for library synthesis in drug discovery.
Co-reporter:Yun He;Li-Li Chen
Journal of Chemical Crystallography 2008 Volume 38( Issue 1) pp:27-31
Publication Date(Web):2008 January
DOI:10.1007/s10870-007-9272-z
7,4′-bis-(hydroxyl)-8,3′,5′-tris-(hydroxymethyl)isoflavone (I) and its ester were synthesized and examined by IR, element analysis and 1H NMR. The crystal of 7,4′-bis-(acetyl oxide)-8,3′,5′-tris-(acetoxymethyl)isoflavone (II) was studied by X-ray diffraction. (II) crystallizes in the monoclinic with space group P21/c. a = 17.987(3) Å, b = 17.972(3) Å, c = 8.4087(11) Å, β = 97.703(3)°, V = 2693.7(6) Å3 and Z = 4. The molecular structure of the ester consists of a benzopyranone moiety, a phenyl moiety, two acetyl oxides and three acetoxymethyl groups. Hydrogen bonds and aromatic stacking interactions link the ester into a two-dimensional structure.
Co-reporter:Li-qun Kou;Xin-Li Cheng
Journal of Chemical Crystallography 2008 Volume 38( Issue 1) pp:21-25
Publication Date(Web):2008 January
DOI:10.1007/s10870-007-9271-0
Two apigenin alkylation derivatives, 4′,7-dimethoxyl-5-hydroxyflavone (I) and 4′,7-diethoxyl-5-hydroxyflavone (II), have been synthesized and their crystal structures were determined by 1H NMR and single crystal X-ray diffraction study. (I) is triclinic, space group P−1 with a = 7.120(5) Å, b = 7.297(5) Å, c = 13.559(10) Å, α = 89.313(12)°, β = 86.298(12)°, γ = 83.999(13)° and Z = 2. (II) is monoclinic, space group P 21/c with a = 16. 309(4) Å, b = 7.303(2) Å, c = 15.185(4) Å, α = 90.00°, β = 115.70(2)°, γ = 90.00° and Z = 4. They have the same flavone skeleton which is composed of a benzopyranone moiety and a phenyl moiety. Molecules of (I) are linked into a two-dimensional network by a combination of C–H···O hydrogen bond and π–π stacking interactions. (II) shows some discrepancies with (I) and the molecules are linked into a column by π–π stacking interaction.
Co-reporter:Zun-Ting Zhang;Xue-Ling Zhang
Journal of Chemical Crystallography 2008 Volume 38( Issue 2) pp:129-133
Publication Date(Web):2008 February
DOI:10.1007/s10870-007-9277-7
Two isoflavone derivatives, 5,6,7,4′-tetramethoxyisoflavone (I) and 6,4′-dimethoxy- 7-ethoxy-5-hydroxylisoflavone (II), have been synthesized and their crystal structures were determined by 1H NMR and single crystal X-ray diffraction studies. I is triclinic, space group P-1 with a = 7.828(1) Å, b = 10.285(2) Å, c = 11.608(2) Å, α = 104.90(2)°, β = 110.546(9)°, γ = 99.54(1)° and Z = 2. II is orthorhombic, space group Pna21 with a = 7.0244(6) Å, b = 15.0104(15) Å, c = 15.7538(15) Å, and Z = 4. Molecules of I are linked into two-dimensional structure by a combination of C–H···O hydrogen bond and F-type aromatic–aromatic interactions. II shows some discrepancies with I and the molecules are linked into columns by T-type aromatic-aromatic interaction.F-type or T-type Aromatic–Aromatic Interaction in Two Isoflavone DerivativesZun-Ting Zhang,* Xue-Ling Zhang
Co-reporter:Xue-Ling Zhang;Yong Liang
Journal of Chemical Crystallography 2008 Volume 38( Issue 11) pp:861-865
Publication Date(Web):2008 November
DOI:10.1007/s10870-008-9406-y
[Na(H2O)2(C18H15O6SO3)]2 was synthesized by sulfated 5-hydroxy-6,7,4′-trimethoxyisoflavone with concentrated sulfuric acid. Single-crystal X-ray diffraction study indicates that it is a dimeric centrosymmetric species. The coordination polyhedron of each Na(I) atom exhibits a distorted trigonal bipyramidal geometry. The dimeric units are linked by intermolecular hydrogen bonds C–H⋯π, C–H⋯O and O–H⋯O to result in a three-dimensional framework.[Na(H2O)2(C18H15O6SO3)]2 was synthesized by sulfated 5-hydroxy-6,7,4′-trimethoxyisoflavone with concentrated sulfuric acid. The coordination polyhedron of each Na(I) atom exhibits a distorted trigonal bipyramidal geometry. The dimeric centrosymmetric units are linked by intermolecular hydrogen bonds C–H⋯π, C–H⋯O and O–H⋯O to result in a three-dimensional framework.Open image in new window
Co-reporter:Zun-Ting Zhang;Da-Jin Tan;Dong Xue
Helvetica Chimica Acta 2007 Volume 90(Issue 11) pp:2096-2108
Publication Date(Web):16 NOV 2007
DOI:10.1002/hlca.200790217
An efficient protocol has been developed for the preparation of a series of new 3,4-diaryl-1H-pyrazoles, potential pharmacological and agricultural targets, by the reaction of hydrazine hydrate with different natural isoflavones or their derivatives. The target compounds were obtained in good-to-excellent yields (80–95%; Table 2) under fairly mild reaction conditions (80°) tolerating various functional groups. The new compounds were fully characterized, and the single-crystal X-ray structures of 3,5-diethoxy-2-[4-(4-ethoxyphenyl)-1H-pyrazol-3-yl]phenol (26) and of the peracetylated compound 2-{1-acetyl-4-[4-acetoxy-3-(diacetylamino)phenyl]-1H-pyrazol-3-yl}-5-acetoxyphenyl acetate (35) were solved (Figure).
Co-reporter:Juanjuan Wang, Zunting Zhang, Wenli Wang and Fangfang Liu
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 12) pp:NaN2038-2038
Publication Date(Web):2013/01/22
DOI:10.1039/C3OB27247H
The one-step cyclocondensation of substituted isoflavones with cyanothioacetamide in the presence of sodium hydroxide gave an array of 3-cyano-5,6-diaryl pyridine-2(1H)-thiones in good yields. The procedure involves base-mediated ring opening of the isoflavones and subsequent Knoevenagel condensation between the 1,3-dicarbonyl intermediate generated from the isoflavones and cyanothioacetamide, followed by ring closure and dehydration.