4-(3-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)thieno[3,2-d]pyrimidine

Noh, Eun Sun; Kim, Sung Min; Song, Yang-Heon

doi:10.3390/m1136

Cited by 2 publications

(8 citation statements)

References 19 publications

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“…[17][18][19][20] In 13 C NMR spectrum, compound 3 i possessed characteristic absorptions at δ 155.5 ppm for pyrmidine carbon N = 13 CHÀ N=C. [17][18][19][20] Furthermore, the structure of compound 3 i was also characterized by the single-crystal X-ray diffraction study (ORTEP) presented in Figure 1. By product pyrazolothiazoles 4 a-o were also fully characterized by spectroscopic methods.…”

Section: Resultsmentioning

confidence: 99%

“…(13), 187 (13), 172 (11), 150 (12), 149 (100), 134 (15), 133 (23), 129 (12), 128 (46), 122 (12), 121 (40), 118 (16), 107 (29), 106 (15), 105 (10), 104 (16), 103 (20), 92 (56), 78 (15), 77 (98), 64 (16); HRMS (EI) calcd for C 17 H 14 N 4 OS 322.0888, found 322.0898. (11), 188 (18), 187 (22), 174 (10), 164 (67), 161 (22), 160 (13), 146 (12), 134 (12), 133 (10), 129 (31), 128 (100), 118 (78), 104 (27), 103 (30), 102 (19), 91 (11), 90 (18), 89 (15), 77 (57), 76 (64), 75 (25), 64 (10), 63 (12); HRMS (EI) calcd for C 16 H 11 N 5 O 2 S 337.0633, found 337.0631.…”

Section: -Phenyl-4-thiocyanato-1-(p-tolyl)-1h-pyrazol-5-amine (2 D)mentioning

confidence: 99%

“…77-78 °C; 1 H NMR (400 MHz, DMSO-d 6 ) δ 6.37 (br, 2H, NH 2 ), 7.39-7.44 (m, 1H, ArH), 7.53(d, J = 4.16 Hz, 4H), 7.67 (s, 1H); 13 (25), 127 (11), 126 (12), 85 (12), 57 (36), 52 (18); HRMS (EI) calcd for C 5 H 6 N 4 S 154.0313, found 154.0320. (13), 140 (19), 135 (21), 71 (10), 66 (19), 57 (55); HRMS (EI) calcd for C 6 H 8 N 4 S 168.0470, found 168.0462.…”

Section: -Phenyl-4-thiocyanato-1h-pyrazol-5-amine (2 K)mentioning

confidence: 99%

“…(10), 264 (10), 214 (15), 188 (50), 187 (51), 160 (10), 130 (26), 117 (38), 104 (12), 91 (65), 90 (10), 89 (11), 86 (36), 84 (20), 77 (13), 69 (12), 66 (24), 65 (16), 57 (49); HRMS (EI) m/z: [M] + calcd for C 17 H 13 N 3 S 291.0830, found 291.0829. 20), 291 (M + , 100), 290 (20), 161 (19), 117 (18), 91 (23); HRMS (EI) calcd for C 17 H 13 N 3 S 291.0830, found 291.0826.…”

Section: Standard Procedures For Synthesis Of Pyrazolo[34-d]pyrimidin...mentioning

confidence: 99%

“…[10][11][12][13][14] One-pot reaction (Route A and B in Scheme 1) [15] and microwave-assisted/solvent free synthesis (Route C in Scheme 1) [16] possess significant advantages and are widely considered as powerful tools in synthetic chemistry and reaction design approaches. Previously, we have developed efficient one-pot reaction and/or microwave-assisted synthesis method of pyrazolo [3,4-d]pyrimidines by treating 5-aminopyrazoles or 1H-pyrazol-5-yl-N,N-dimethyl-formamidines with formamide or DMF as well as, PBr 3 or POCl 3 as a coupling agent (Route A [17,18] and B [19,20] in Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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One‐pot Microwave‐assisted Synthesis of Pyrazolopyrimidines from 5‐Amino‐4‐thiocyanato‐pyrazoles with Vilsmeier Reagent

Zeng,

Chung

et al. 2024

ChemistrySelect

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A facile one‐pot microwave‐assisted synthesis of pyrazolopyrimidines and pyrazolothiazoles was developed by reacting 5‐amino‐4‐thiocyanato‐pyrazoles with Vilsmeier Reagent (PBr3/foramide). The reaction gave the corresponding pyrazolopyrimidines as major products in good yields (61–85 %) and pyrazolothiazoles as minor products (11–23 % yields). The plausible reaction mechanism was proposed to account for the transformation of pyrazolopyrimidines and pyrazolothiazoles through two paths A and B. In path A, the reaction leading to the formation of pyrazolopyrimidines proceeded through four sequential steps, including acidic catalyzed cascade dethiocyanation/cyclization, Vilsmeier reaction, ring expansion, and deamination. The formation of the pyrazolothiazole in path B was caused by the nucleophilic heterocyclization reaction involving the sulfur nucleophilic reaction of thiocyanate (R−SC≡N) and the departure of a cyanamide. Based on the experimental results, we observed that the path A for the formation of pyrazolopyrimidines was more favorable.

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