SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 8, 2008, Pages 1129-1132

An efficient one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives

(3) Ghahremanzadeh, Ramin a Shakibaei, Ghazaleh Imani a Bazgir, Ayoob a

a SHAHID BEHESHTI UNIVERSITY (Iran)

Author keywords

Ethyl cyanoacetate; Malononitrile; Phthalhydrazide; Pyrazolo 1,2 b phthalazine 5 dione

Indexed keywords

3 AMINO 1 (2 CHLOROPHENYL)5,10 DIHYDRO 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBONITRILE; 3 AMINO 1 (4 CHLOROPHENYL) 5,10 DIHYDRO 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBONITRILE; 3 AMINO 5,10 DIHYDRO 5,10 DIOXO 1 PHENYL 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBONITRILE; ACETIC ACID DERIVATIVE; ALDEHYDE; ETHYL 3 AMINO 5,10 DIHYDRO 1 (3 NITROPHENYL) 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBOXYLATE; ETHYL 3 AMINO 5,10 DIHYDRO 1 (4 NITROPHENYL) 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBOXYLATE; ETHYL 3 AMINO 5,10 DIHYDRO 5,10 DIOXO 1 PARA TOLYL 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBOXYLATE; HYDRAZIDE DERIVATIVE; MALONALDEHYDE; PHTHALAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 44349108844 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072716 Document Type: Article

Times cited : (159)

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- Typical Procedure for the Preparation of 3-Amino-5,10-dihydro-5,10- dioxo-1-phenyl-1H-pyrazolo[1,2-b] phthalazin-2-carbonitrile (7a) A mixture of malononitrile (1 mmol, phthalhydrazide (1 mmol, benzaldehyde (1 mmol, PTSA (0.3 mmol, and [bmim]Br (0.30 g) was heated at 100°C for 3 h (TLC, After cooling, the reaction mixture was washed with H2O (15 mL) and residue recrystallized from MeOH to afford the pure product 7a. Yellow powder (94, mp 276-278°C. IR (KBr, νmax, 3359, 3190, 2197, 1690, 1658 cm-1. MS (EI, 70 eV, m/z, 316 (20, M, 299 (42, 239 (100, 1H NMR (300 MHz, DMSO-d6, δ, 6.13 (1 H, s, CH, 7.29-7.47 (5 H, m, ArH, 7.93-8.26 (4 H, m, ArH, 8.09 (2 H, s, NH2) ppm. 13C NMR 75 MHz, DMSO-d 6, δ, 62.4, 63.6, 116.1, 127.2, 127.3, 127.7, 128.7, 128.9, 129.2, 134.1, 135.1, 138.7
- 2: C, 68.35; H, 3.82; N, 17.71. Found: C, 68.41; H, 3.87; N, 17.78.

27
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- Selected Characterization Data 3-Amino-1-(2-chlorophenyl)-5,10- dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile (7b) Yellow powder (88, mp 259-262°C. IR (KBr, νmax, 3370, 3176, 2207, 1695, 1658 cm-1. MS (EI, 70 eV, m/z, 350 (17, M, 333 (44, 239 (100, 1H NMR (300 MHz, DMSO-d6, δ, 6.46 (1 H, s, CH, 7.33-7.62 (4 H, m, ArH, 7.87-8.30 (4 H, m, ArH, 8.15 (2 H, s, NH2) ppm. 13C NMR (75 MHz, DMSO-d6, δ, 60.2, 61.0, 116.2, 127.2, 127.8, 128.3, 128.8, 129.2, 130.2, 130.4, 131.7, 134.3, 135.2, 135.8, 151.6, 154.0, 157.1 ppm. Anal. Calcd, ) for C18H11ClN 4O2: C, 61.64; H, 3.16; N, 15.97. Found: C, 61.57; H, 3.11; N, 15.91. 3-Amino-1-(4-chlorophenyl)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile (7c) Yellow
- 4: C, 66.83; H, 5.07; N, 11.13. Found: C, 66.88; H, 5.01; N, 11.19.

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