HRP20160381T1 - Postupak za stereoselektivnu pripravu pirazol karboksamida - Google Patents
Postupak za stereoselektivnu pripravu pirazol karboksamida Download PDFInfo
- Publication number
- HRP20160381T1 HRP20160381T1 HRP20160381TT HRP20160381T HRP20160381T1 HR P20160381 T1 HRP20160381 T1 HR P20160381T1 HR P20160381T T HRP20160381T T HR P20160381TT HR P20160381 T HRP20160381 T HR P20160381T HR P20160381 T1 HRP20160381 T1 HR P20160381T1
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- Croatia
- Prior art keywords
- formula
- compound
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- enantioselective
- reagent
- Prior art date
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- 238000000034 method Methods 0.000 title claims 10
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 title 1
- 230000000707 stereoselective effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 17
- 239000003153 chemical reaction reagent Substances 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229910052707 ruthenium Inorganic materials 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- VCHDBLPQYJAQSQ-LOYHVIPDSA-N [(4s,5s)-5-(diphenylphosphanylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-diphenylphosphane Chemical compound C([C@H]1OC(O[C@@H]1CP(C=1C=CC=CC=1)C=1C=CC=CC=1)(C)C)P(C=1C=CC=CC=1)C1=CC=CC=C1 VCHDBLPQYJAQSQ-LOYHVIPDSA-N 0.000 claims 1
- MXGXXBYVDMVJAO-UHFFFAOYSA-N [1-[2-bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical group CC1=CC(C)=CC(P(C=2C=C(C)C=C(C)C=2)C=2C(=C3C=CC=CC3=CC=2)C=2C3=CC=CC=C3C=CC=2P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 MXGXXBYVDMVJAO-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- -1 oxygen oxime Chemical class 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 claims 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
- C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/573—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/693—Unsaturated compounds containing a keto groups being part of a ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/743—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups having unsaturation outside the rings, e.g. humulones, lupulones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catalysts (AREA)
Claims (13)
1. Postupak za enantioselektivnu pripravu ((1S,4R)-9-diklorometilen-1,2,3,4-tetrahidro-1,4-metano-naftalen-5-il)-amida 3-difluorometil-1-metil-1H-pirazol-4-karboksilne kiseline s formulom Ib
[image]
naznačen time da navedeni postupak sadrži
a) redukciju spoja s formulom II
[image]
s enantioselektivnim reagensom u spoj s formulom IIIe
[image]
b) dehidraciju spoja s formulom IIIe u prisutnosti kiseline u spoj s formulom IVa
[image]
c) reakciju spoja s formulom IVa s hidroksilaminom u spoj s formulom Va
[image]
i
d) aciliranje oksima kisika spoja s formulom Va u prisutnosti otapala i sredstvom za aciliranje i konačno reakciju nastalog produkta sa spojem s formulom VI
[image]
e) reakciju spoja s formulom V sa suviškom spoja s formulom VI.
2. Postupak prema zahtjevu 1, naznačen time da se enantioselektivna redukcija spoja s formulom II provodi pomoću hidrogeniranja u prisutnosti katalizatora prijelaznog metala.
3. Postupak prema zahtjevu 1, naznačen time da se enantioselektivna redukcija spoja s formulom II provodi pomoću transfer hidrogeniranja u prisutnosti katalizatora prijelaznog metala.
4. Postupak prema zahtjevu 1, naznačen time da enantioselektivni reagens je rutenijev katalizator.
5. Postupak prema zahtjevu 2, naznačen time da enantioselektivni reagens je rutenijev katalizator.
6. Postupak prema zahtjevu 3, naznačen time da enantioselektivni reagens je rutenijev katalizator.
7. Postupak prema zahtjevu 1, naznačen time da enantioselektivni reagens je kloro{(R)-(+)-2,2'-bis[di(3,5-ksilil)fosfino]-1,1'-binaftil}[(2R)-(-)-1-(4-metoksifenil)-1'-(4-metoksifenil-kC)-3-metil-1,2-butandiamin]rutenij(II).
8. Postupak prema zahtjevu 1, naznačen time da enantioselektivni reagens je dikloro[(4S,5S)-(+)-4,5-bis(difenilfosfinometil)-2,2-dimetil-1,3-dioksolan][(S)-(-)-2-(α-metilmetanamin)-1 H-benzimidazol]rutenij(II)
9. Spoj (1S,4R)-9-diklorometilen-8-hidroksi-oktahidro-1,4-metano-naftalen-5-on s formulom IIIe
[image]
i njegovi izomeri s formulama IIIf do IIIm:
[image]
[image]
[image]
10. Spoj (1S,4R)-9-diklorometilen-2,3,4,6,7,8-heksahidro-1H-1,4-metanonaftalen-5-on s formulom
[image]
i njegovi izomeri s formulama IVb, IVc i IVd:
[image]
11. Spoj (1S,4R)-9-diklorometilen-2,3,4,6,7,8-heksahidro-1H-1,4-metano-naftalen-5-on oksim s formulom Va
[image]
i njegovi izomeri s formulama Vb, Vc i Vd:
[image]
12. Spoj s formulom XXIIIa
[image]
naznačen time da X je kisik ili sumpor, R1 je C1-C6alkoksi, CH3-C(=CH2)-O-, fenoksi ili triklorometoksi.
13. Spoj s formulom XXIVa
[image]
naznačen time da X je kisik ili sumpor.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12155526 | 2012-02-15 | ||
| EP12173642 | 2012-06-26 | ||
| EP12177606 | 2012-07-24 | ||
| EP12182799 | 2012-09-03 | ||
| PCT/EP2013/052803 WO2013120860A1 (en) | 2012-02-15 | 2013-02-13 | Process for the stereoselective preparation of a pyrazole carboxamide |
| EP13703616.6A EP2814813B1 (en) | 2012-02-15 | 2013-02-13 | Process for the stereoselective preparation of a pyrazole carboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160381T1 true HRP20160381T1 (hr) | 2016-05-20 |
Family
ID=47683767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160381TT HRP20160381T1 (hr) | 2012-02-15 | 2016-04-13 | Postupak za stereoselektivnu pripravu pirazol karboksamida |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9120759B2 (hr) |
| EP (1) | EP2814813B1 (hr) |
| JP (1) | JP6216332B2 (hr) |
| KR (1) | KR102037942B1 (hr) |
| CN (1) | CN104114539B (hr) |
| AP (1) | AP4027A (hr) |
| AR (1) | AR089989A1 (hr) |
| AU (1) | AU2013220443B2 (hr) |
| BR (1) | BR112014020011B1 (hr) |
| CA (1) | CA2863725C (hr) |
| CO (1) | CO7030966A2 (hr) |
| EA (1) | EA026529B1 (hr) |
| ES (1) | ES2568638T3 (hr) |
| HR (1) | HRP20160381T1 (hr) |
| HU (1) | HUE028544T2 (hr) |
| PL (1) | PL2814813T3 (hr) |
| RS (1) | RS54672B1 (hr) |
| TW (1) | TWI510472B (hr) |
| UY (1) | UY34626A (hr) |
| WO (1) | WO2013120860A1 (hr) |
| ZA (1) | ZA201405565B (hr) |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5093347A (en) | 1991-01-28 | 1992-03-03 | Monsanto Company | 3-difluoromethylpyrazolecarboxamide fungicides, compositions and use |
| JP4004123B2 (ja) | 1997-12-26 | 2007-11-07 | 独立行政法人科学技術振興機構 | ルテニウム錯体を触媒とするアルコール化合物の製造方法 |
| WO2004007506A1 (ja) | 2002-07-15 | 2004-01-22 | Nippon Soda Co.,Ltd. | ルテニウム化合物、ジアミン配位子および光学活性アルコールの製造方法 |
| ITPD20040115A1 (it) | 2004-05-04 | 2004-08-04 | Univ Degli Studi Udine | Complessi di rutenio con 2-(amminometil)piridine e fosfine, loro preparazione ed uso come catalizzatori |
| CN1331874C (zh) | 2005-01-27 | 2007-08-15 | 中国科学院上海有机化学研究所 | 过渡金属络合物、合成方法及其用途 |
| CN101296913B (zh) | 2005-10-25 | 2013-02-13 | 先正达参股股份有限公司 | 用作杀微生物剂的杂环酰胺衍生物 |
| CN101328191B (zh) * | 2008-06-13 | 2013-06-05 | 中国科学院上海有机化学研究所 | 一类含氮配体过渡金属络合物、合成方法及其用途 |
| BRPI0920833B1 (pt) * | 2008-10-27 | 2018-02-06 | Syngenta Participations Ag | Preparação de benzonorborbenos |
| GEP20146010B (en) * | 2009-08-06 | 2014-01-10 | Syngenta Participations Ag | Method of pyrazole carboxylic acid amides preparation |
| ES2535469T3 (es) | 2010-04-28 | 2015-05-11 | Takasago International Corporation | Complejo de rutenio y procedimiento de preparación un compuesto de alcohol ópticamente activo |
| AR083987A1 (es) | 2010-12-01 | 2013-04-10 | Bayer Cropscience Ag | Amidas de acido pirazolcarboxilico utiles para la reduccion de la contaminacion de micotoxina en las plantas |
| TWI534126B (zh) | 2011-01-25 | 2016-05-21 | 先正達合夥公司 | 用於製備吡唑羧酸醯胺之方法 |
-
2013
- 2013-02-08 TW TW102105147A patent/TWI510472B/zh active
- 2013-02-13 AU AU2013220443A patent/AU2013220443B2/en active Active
- 2013-02-13 AP AP2014007855A patent/AP4027A/en active
- 2013-02-13 CA CA2863725A patent/CA2863725C/en active Active
- 2013-02-13 WO PCT/EP2013/052803 patent/WO2013120860A1/en active Application Filing
- 2013-02-13 HU HUE13703616A patent/HUE028544T2/en unknown
- 2013-02-13 CN CN201380009535.9A patent/CN104114539B/zh active Active
- 2013-02-13 BR BR112014020011-4A patent/BR112014020011B1/pt active IP Right Grant
- 2013-02-13 KR KR1020147025495A patent/KR102037942B1/ko active IP Right Grant
- 2013-02-13 EA EA201400904A patent/EA026529B1/ru not_active IP Right Cessation
- 2013-02-13 EP EP13703616.6A patent/EP2814813B1/en active Active
- 2013-02-13 RS RS20160240A patent/RS54672B1/en unknown
- 2013-02-13 ES ES13703616.6T patent/ES2568638T3/es active Active
- 2013-02-13 PL PL13703616T patent/PL2814813T3/pl unknown
- 2013-02-13 JP JP2014557014A patent/JP6216332B2/ja active Active
- 2013-02-13 US US14/373,439 patent/US9120759B2/en active Active
- 2013-02-14 UY UY0001034626A patent/UY34626A/es active IP Right Grant
- 2013-02-14 AR ARP130100454A patent/AR089989A1/es active IP Right Grant
-
2014
- 2014-07-28 ZA ZA2014/05565A patent/ZA201405565B/en unknown
- 2014-08-12 CO CO14175214A patent/CO7030966A2/es unknown
-
2016
- 2016-04-13 HR HRP20160381TT patent/HRP20160381T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW201345897A (zh) | 2013-11-16 |
| BR112014020011A8 (pt) | 2017-07-11 |
| JP6216332B2 (ja) | 2017-10-18 |
| CO7030966A2 (es) | 2014-08-21 |
| AU2013220443B2 (en) | 2016-10-27 |
| RS54672B1 (en) | 2016-08-31 |
| AR089989A1 (es) | 2014-10-01 |
| WO2013120860A1 (en) | 2013-08-22 |
| KR20140128429A (ko) | 2014-11-05 |
| EA026529B1 (ru) | 2017-04-28 |
| UY34626A (es) | 2013-09-30 |
| US9120759B2 (en) | 2015-09-01 |
| CN104114539A (zh) | 2014-10-22 |
| EA201400904A1 (ru) | 2015-01-30 |
| EP2814813A1 (en) | 2014-12-24 |
| AU2013220443A1 (en) | 2014-08-28 |
| BR112014020011A2 (hr) | 2017-06-20 |
| CN104114539B (zh) | 2016-10-12 |
| PL2814813T3 (pl) | 2016-07-29 |
| AP2014007855A0 (en) | 2014-08-31 |
| EP2814813B1 (en) | 2016-02-10 |
| AP4027A (en) | 2017-02-04 |
| US20140364622A1 (en) | 2014-12-11 |
| BR112014020011B1 (pt) | 2019-08-20 |
| JP2015506997A (ja) | 2015-03-05 |
| HUE028544T2 (en) | 2016-12-28 |
| TWI510472B (zh) | 2015-12-01 |
| KR102037942B1 (ko) | 2019-10-29 |
| ES2568638T3 (es) | 2016-05-03 |
| CA2863725A1 (en) | 2013-08-22 |
| CA2863725C (en) | 2019-10-01 |
| ZA201405565B (en) | 2016-01-27 |
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