Grinding and Microwave‐assisted Synthesis of Heterocyclic Molecules in High Yields and Their Biological Evaluation

Kumar, Sandeep; Kumar, Anuj; Nikhil, Kumar; Roy, Partha; Sondhi, Sham M.

doi:10.1002/jhet.2481

Cited by 2 publications

(3 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N-Aminophthalimide ( 2a ) [ 42 ]: White solid; 92% yield; mp 202–205 °C; 1 H NMR (DMSO- d 6 , 400 MHz) δ 7.83 (dd, J = 5.8, 3.4 Hz, 2H, Ar H ), 8.05 (dd, J = 5.8, 3.4 Hz, 2H, Ar H ); 13 C NMR (DMSO- d 6 , 100 MHz): δ 123.28 (2 × C), 130.53 (2 × C), 134.81 (2 × C), 167.36 (2 × C); FT-IR (KBr): 3482, 3341, 3262, 3093, 1778, 1719, 1605, 1468, 1409, 1291, 1197, 1091, 1075, 1020, 918, 800, 718, 526 cm −1 ; EIMS m/z : 162 (M + , 100), 105 (12), 104 (74), 77 (12), 76 (26), 50 (11); HRMS (EI) m/z : [M] + Calcd for C 8 H 6 N 2 O 2 : 162.0429; Found: 162.0425.…”

Section: Methodsmentioning

confidence: 99%

“…N-Amino-2,3-pyrazinedicarboxylicphthalimide ( 2d ) [ 42 ]: Brown solid; 82% yield; mp 220–222 °C; 1 H NMR (D 2 O, 400 MHz) δ 8.59 (s, 2H, Ar H ); 13 C NMR (D 2 O, 100 MHz) δ 143.28 (2 × C), 149.18 (2 × C), 172.29 (2 × C); FT-IR (KBr): 3430, 3282, 3164, 2936, 2750, 2636, 1679, 1621, 1353, 1161, 1107, 975, 825 cm −1 . EIMS m/z : 164 (M + , 36), 150 (25), 124 (40), 106 (76), 80 (100), 79 (30), 78 (56), 53 (69), 52 (95), 51 (52).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Structural Identification between Phthalazine-1,4-Diones and N-Aminophthalimides via Vilsmeier Reaction: Nitrogen Cyclization and Tautomerization Study

Chung

Tseng

et al. 2021

Molecules

View full text Add to dashboard Cite

N-aminophthalimides and phthalazine 1,4-diones were synthesized from isobenzofuran-1,3-dione, isoindoline-1,3-dione, furo [3,4-b] pyrazine-5,7-dione, or 1H-pyrrolo [3,4-c] pyridine-1,3-dione with monohydrate hydrazine to carry out the 5-exo or 6-endo nitrogen cyclization under the different reaction conditions. Based on the control experimental results, 6-endo thermodynamic hydrohydrazination and kinetical 5-exo cyclization reactions were individually selective formation. Subsequently, Vilsmeier amidination derivatization was successfully developed to probe the structural divergence between N-aminophthalimide 2 and phthalazine 1,4-dione 3. On the other hand, the best tautomerization of N-aminophthalimide to diazinone was also determined under acetic acid mediated solution.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Structural Identification between Phthalazine-1,4-Diones and N-Aminophthalimides via Vilsmeier Reaction: Nitrogen Cyclization and Tautomerization Study

Chung

Tseng

et al. 2021

Molecules

View full text Add to dashboard Cite

show abstract

“…Sondhi et al designed a simple and eco-friendly reaction protocol for the synthesis of azomethine and amidine derivatives of isoindole and pyrrolopyrazine from different dicarboxylic acids 77 (cis cyclohexane 1,2-dicarboxylic acid, phthalic acid and pyrazine 2,3-dicarboxylic acid) and hydrazine hydrate (Scheme 25). 34 First of all 2-aminohexahydro-1H-isoindole-1,3(2H)-dione, 2-amino-1H-isoindole-1,3(2H)-dione and 6amino-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione were generated from dicarboxylic acids and hydrazine hydrate through grinding followed by microwave irradiation with aldehydes and different pyridines to generate the corresponding azomethine and amidine derivatives of isoindole and pyrrolopyrazine with excellent yields. Pharmacological studies revealed that the newly synthesised compounds possess both good anti-inammatory and anti-cancer activity.…”

Section: Microwave Assisted Synthesis Of Indolesmentioning

confidence: 99%