دورية أكاديمية
Synthesis of 4-substituted chlorophthalazines, dihydrobenzoazepinediones, 2-pyrazolylbenzoic acid, and 2-pyrazolylbenzohydrazide via 3-substituted 3-hydroxyisoindolin-1-ones.
| العنوان: | Synthesis of 4-substituted chlorophthalazines, dihydrobenzoazepinediones, 2-pyrazolylbenzoic acid, and 2-pyrazolylbenzohydrazide via 3-substituted 3-hydroxyisoindolin-1-ones. |
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| المؤلفون: | Nguyen HN; Department of Chemistry Research and Discovery, Amgen Inc., 360 Binney St., Cambridge, Massachusetts 02142, USA. hanhn@amgen.com, Cee VJ, Deak HL, Du B, Faber KP, Gunaydin H, Hodous BL, Hollis SL, Krolikowski PH, Olivieri PR, Patel VF, Romero K, Schenkel LB, Geuns-Meyer SD |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2012 Apr 20; Vol. 77 (8), pp. 3887-906. Date of Electronic Publication: 2012 Apr 05. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مواضيع طبية MeSH: | Benzoates/*chemical synthesis , Benzoates/*chemistry , Hydrazines/*chemical synthesis , Hydrazines/*chemistry , Isoindoles/*chemical synthesis , Isoindoles/*chemistry , Phthalazines/*chemical synthesis , Phthalazines/*chemistry , Phthalimides/*chemistry , Pyrazoles/*chemical synthesis , Pyrazoles/*chemistry, Catalysis ; Halogenation ; Molecular Structure ; Stereoisomerism |
| مستخلص: | Herein we describe a general three-step synthesis of 4-substituted chlorophthalazines in good overall yields. In the key step, N,N-dimethylaminophthalimide (8a) directs the selective monoaddition of alkyl, aryl, and heteroaryl organometallic reagents to afford 3-substituted 3-hydroxyisoindolinones 9b, 9i-9am. Many of these hydroxyisoindolinones are converted to chlorophthalazines 1b-1v via reaction with hydrazine, followed by chlorination with POCl(3). We have also discovered two novel transformations of 3-vinyl- and 3-alkynyl-3-hydroxyisoindolinones. Addition of vinyl organometallic reagents to N,N-dimethylaminophthalimide (8a) provided dihydrobenzoazepinediones 15a-15c via the proposed ring expansion of 3-vinyl-3-hydroxyisoindolinone intermediates. 3-Alkynyl-3-hydroxyisoindolinones react with hydrazine and substituted hydrazines to afford 2-pyrazolyl benzoic acids 16a-16d and 2-pyrazolyl benzohydrazides 17a-17g rather than the expected alkynyl phthalazinones. (© 2012 American Chemical Society) |
| المشرفين على المادة: | 0 (2-pyrazolylbenzohydrazide) 0 (2-pyrazolylbenzoic acid) 0 (Benzoates) 0 (Hydrazines) 0 (Isoindoles) 0 (N,N-dimethylaminophthalimide) 0 (Phthalazines) 0 (Phthalimides) 0 (Pyrazoles) |
| تواريخ الأحداث: | Date Created: 20120331 Date Completed: 20120801 Latest Revision: 20121115 |
| رمز التحديث: | 20221213 |
| DOI: | 10.1021/jo3000628 |
| PMID: | 22458369 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6904 |
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| DOI: | 10.1021/jo3000628 |