公开(公告)号：KR101519011B1

公开(公告)日：2015-05-11

申请号：KR1020140001717

申请日：2014-01-07

Applicant: 강원대학교산학협력단

Inventor： 이구연 ,  이필호 ,  김재현 ,  박정민 ,  윤지희

IPC: C07D493/04 ,  A61K31/37 ,  A61P31/00 ,  A61P29/00

Abstract: 본발명은비스무트촉매를이용한피라노쿠마린유도체의제조방법에관한것으로서, 프로파질알코올화합물과 4-하이드록시쿠마린화합물을비스무트트리플레이트촉매의존재하에서반응시켜피라노[3,2-]쿠마린유도체를제조하는것을특징으로한다. 상기한본 발명에따른피라노쿠마린유도체의제조방법은종래강산을사용하는경우부산물이다량발생하여수율이떨어지는단점을보완할수 있을뿐만아니라반응단계를간소화하여높은수율로피라노[3,2-]쿠마린유도체를제조할수 있는장점이있다.

Abstract translation: 本发明涉及使用铋催化剂制备吡喃香豆素衍生物的方法。 更具体地，吡喃并[3,2-c]香豆素衍生物是通过在三氟甲磺酸铋催化剂的存在下使炔丙醇化合物与4-羟基香豆素化合物反应制备的。 根据本发明，该方法可以解决现有方法的缺点，即由于使用产生大量副产物的强酸，产率低。 此外，该方法包括简化的反应步骤。 因此，可以通过该方法以高产率制备吡喃并[3,2-c]香豆素衍生物。

公开(公告)号：KR101387060B1

公开(公告)日：2014-04-18

申请号：KR1020130010298

申请日：2013-01-30

Applicant: 강원대학교산학협력단

Inventor： 이구연 ,  이필호 ,  박정민 ,  윤지희

IPC: C07C45/37 ,  C07C49/76 ,  B01J23/745

Abstract: The present invention relates to a production method of a ketone compound which includes a step of making an alkyne compound react under the presence of an iron catalyst and a sulfonic acid based compound, thereby simplifying a reaction step compare to existing production methods, removing the generation of byproducts, and allowing the production of the ketone compound with high purity and high yield.

Abstract translation: 本发明涉及一种酮化合物的制造方法，其包括在铁催化剂和磺酸系化合物的存在下使炔化合物反应的步骤，从而与现有的制造方法相比，简化了反应步骤，除去了一代 的副产物，并且能够以高纯度和高产率生产酮化合物。

公开(公告)号：KR101220148B1

公开(公告)日：2013-01-15

申请号：KR1020120048080

申请日：2012-05-07

Applicant: 강원대학교산학협력단

Inventor： 이필호 ,  박성국 ,  박영철

IPC: C07D231/12 ,  B01J23/44

Abstract: PURPOSE: A pyrazole derivative and a method for preparing the same are provided to be used as an important intermediate, and to synthesize a precision chemistry intermediate including agrochemicals. CONSTITUTION: A method for preparing a pyrazole derivative of chemical formula 1 comprises: a step of intramolecular cyclizing hydrazinecarboxylate derivatives of chemical formula 7 under the presence of TfOH, AuCl, AuCl_3, AuBr_3, Ph_3PAuCl, (C_6F_5)_3PAuCl, (4-CF_3-C_6H_4)_3PAuCl, (IPr)AuCl [IPr = N,N`-bis(2,6-diisopropylphenyl) imidazol-2-ylidine], (IMes)AuCl [IMes = N,N`-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene], (IMes)AuCl [IMes = N,N`-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene], AgNTf_2, AgOTf, AgSbF_6, AgAsF_6, AgPF_6 AgBF_4, AgNO_3, or AgClO_4 catalyst to prepare a 1,2-dihydro-pyrazol-3-one derivative of chemical formula 6; a step of reacting the derivative of chemical formula 6 with N-phenylbis(trifluoro methane sulfominide)(PhNTf_2) under the presence of a base to prepare a pyrazole triflate derivative of chemical formula 2; and a step of reacting the derivative of chemical formula 2 with an boronic acid derivative of chemical formula 3, a terminal alkyne derivative of chemical formula 4, or an organotin compound of chemical formula 5 under the presence of a palladium catalyst.

Abstract translation: 目的：提供吡唑衍生物及其制备方法作为重要的中间体，并合成含有农药的精密化学中间体。 构成：制备化学式1的吡唑衍生物的方法包括：在TfOH，AuCl，AuCl_3，AuBr_3，Ph_3PAuCl，（C_6F_5）_3PAuCl，（4-CF_3-）的存在下，分子内环化化学式7的肼甲酸酯衍生物的步骤， C 6 H 4）_3PAuCl，（IPr）AuCl [IPr = N，N'-双（2,6-二异丙基苯基）咪唑-2-基]]，（IMes）AuCl [IMes = N，N'-双 （三甲基苯基）咪唑-2-亚基]，（IMes）AuCl [IMes = N，N'-双（2,4,6-三甲基苯基）咪唑-2-亚基]，AgNTf_2，AgOTf，AgSbF_6，AgAsF_6，AgPF_6 AgBF_4， AgNO_3或AgClO_4催化剂以制备化学式6的1,2-二氢 - 吡唑-3-酮衍生物; 使化学式6的衍生物与N-苯基双（三氟甲烷砜）（PhNTf_2）在碱存在下反应，制备化学式2的吡唑三氟甲磺酸酯衍生物的步骤; 以及使化学式2的衍生物与化学式3的硼酸衍生物，化学式4的末端炔衍生物或化学式5的有机锡化合物在钯催化剂存在下反应的步骤。

公开(公告)号：KR101150970B1

公开(公告)日：2012-06-08

申请号：KR1020090132449

申请日：2009-12-29

Applicant: 강원대학교산학협력단

Inventor： 김진호 ,  이광무 ,  강동진 ,  이필호

IPC: C07C69/612 ,  C07C69/54 ,  C07C67/333

Abstract: [상기화학식 1에서 R내지 R은각각발명의상세한설명에서정의한바와같다.]

公开(公告)号：KR101087206B1

公开(公告)日：2011-11-29

申请号：KR1020090020852

申请日：2009-03-11

Applicant: 강원대학교산학협력단

Inventor： 이필호 ,  김선대

IPC: C07D311/10 ,  C07D311/04

Abstract: 본 발명은 하기 화학식 1로 표시되는 새로운 쿠마린 유도체 및 이의 제조방법에 관한 것이다.

본 발명에 따른 쿠마린 유도체 제조방법은 산 존재 하에 알레노에이트 화합물과, 알콕시벤젠, 알콕시벤젠 유도체, 디히드록시벤젠, 디히드록시벤젠 유도체로부터 선택되는 1종 이상 화합물을 반응시켜 높은 수율로 쿠마린 유도체를 제조할 수 있는 장점이 있다.
트리플루오로메탄설폰산, 에틸 알레노에이트, 다이메톡시벤젠, 다이메톡시벤젠 유도체, 트라이메톡시벤젠, 트라이메톡시벤젠 유도체, 다이하이드록시벤젠, 다이하이드록시벤젠 유도체, 트리하이드록벤젠, 트리하이드록벤젠 유도체, 쿠마린 유도체

公开(公告)号：KR101069761B1

公开(公告)日：2011-10-05

申请号：KR1020080137304

申请日：2008-12-30

Applicant: 강원대학교산학협력단

Inventor： 이필호 ,  류태규

IPC: C07D307/64

Abstract: 상기화학식 1에서, R, R, R및 R는각각발명의상세한설명에서정의한바와같다.

公开(公告)号：KR101029091B1

公开(公告)日：2011-04-13

申请号：KR1020100032177

申请日：2010-04-08

Applicant: 강원대학교산학협력단

Inventor： 이필호 ,  김상혁 ,  김진식 ,  배준성 ,  오수성 ,  황훈 ,  신두섭

IPC: C07D307/26 ,  C07D307/28

Abstract: PURPOSE: A method for preparing dihydrofuran derivative is provided to selectively prepare dihydrofuran derivative with high yield by a simple test. CONSTITUTION: A dihydrofuran derivative of chemical formula 1 is prepared by intramolecular cyclization of alenyl alcohol derivative of chemical formula 2 under the presence of a cupper salt catalyst of CuCl, CuBr, CuI, CuOTf, Cu(OTf)2, CuCl2, CuBr2, CuI_2, or Cu(OAc)_2, or solvent of N,N-dimethylformamide(DMF), or N,N-dimethylaceteamide(DMA). The organic solvent is dichloromethane(DCM), dichloroethane(DCE), toluene, acetonitrile(MeCN), nitromethane, tetrahydrofuran(THF), N,N-dimehtylformamide(DMF), or N,N-dimethylaceteamide(DMA).

Abstract translation: 目的：提供制备二氢呋喃衍生物的方法，通过简单的试验选择性地制备二氢呋喃衍生物，产率高。 构成：化学式1的二氢呋喃衍生物通过在CuCl，CuBr，CuI，CuOTf，Cu（OTf）2，CuCl 2，CuBr 2，CuI 2的铜盐催化剂存在下，通过化学式2的烯丙醇衍生物的分子内环化制备 ，或Cu（OAc）2，或N，N-二甲基甲酰胺（DMF）或N，N-二甲基乙酰胺（DMA）的溶剂。 有机溶剂是二氯甲烷（DCM），二氯乙烷（DCE），甲苯，乙腈（MeCN），硝基甲烷，四氢呋喃（THF），N，N-二甲基甲酰胺（DMF）或N，N-二甲基乙酰胺（DMA）。

公开(公告)号：KR101013147B1

公开(公告)日：2011-02-10

申请号：KR1020080137331

申请日：2008-12-30

Applicant: 강원대학교산학협력단

Inventor： 이필호 ,  류태규

IPC: C07C321/04

Abstract: 본 발명은 유기 황-인듐 착물을 이용한 신규의 알레닐 설파이드 유도체와 이의 제조방법에 관한 것으로서, 더욱 상세하게는 본 발명은 싸이올 (thiol)의 친핵성을 증가시키기 위해 새로운 형태의 반응 시약인 인듐 트라이(오가노싸이올레이트)와 삼차 프로파질 아세테이트가 교차-짝지움 반응을 하여 제조된 하기 화학식 1로 표시되는 신규의 알레닐 설파이드 유도체와 이의 제조방법에 관한 것이다.
[화학식 1]

상기 화학식 1에서, R
1 , R
2 , R
3 , R
4
는 각각 발명의 상세한 설명에서 정의한 바와 같다.
알레닐 설파이드, 프로파질 아세테이트, 인듐 트라이(오가노싸이올레이트), 팔라듐, 교차-짝지움 반응

公开(公告)号：KR1020100078918A

公开(公告)日：2010-07-08

申请号：KR1020080137304

申请日：2008-12-30

Applicant: 강원대학교산학협력단

Inventor： 이필호 ,  류태규

IPC: C07D307/64

Abstract: PURPOSE: A method for manufacturing a novel furan using organic sulfur-indium complex is provided to use as a raw ingredient for manufacturing medicinal, agricultural, and natural materials. CONSTITUTION: A furan derivative is denoted by chemical formula 1. A method for preparing the furan derivative comprises: a step of performing cross-pairing reaction and intramolecular cyclization of indium tri(organothiolate) of chemical formula 3 with propazyl acetate derivative of chemical formula 2 under the presence of palladium catalyst and phosphine ligand. The palladium catalyst is Pd_2dba_3CHCl_3, Pd(OAc)_2, (dppf)PdCl_2, Pd(PPh_3)_4, (PPh_3)_2PdCl_2, (DPEphos)PdCl_2, or PdCl_2. The phosphine ligand is bis(2-diphenylphosphynophenyl)ether, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, cyclohexyl diphenyl phosphine, 1-1'-bis(diphenylphosphino)ferrocene, 1,2-bis(diphenylphosphino)ether, 1,3-bis(diphenylphosphino)propane, or triphenylphospane.

Abstract translation: 目的：提供使用有机硫 - 铟络合物制造新型呋喃的方法，用作制造药用，农业和天然材料的原料。 构成：呋喃衍生物由化学式1表示。呋喃衍生物的制备方法包括：使化学式3的三（有机硫酸盐）的铟与有机化学式2的丙酸酯衍生物进行交叉配对反应和分子内环化的步骤 在钯催化剂和膦配体的存在下。 钯催化剂为Pd_2dba_3CHCl_3，Pd（OAc）_2，（dppf）PdCl_2，Pd（PPh_3）_4，（PPh_3）_2PdCl_2，（DPEphos）PdCl_2或PdCl_2。 膦配体是双（2-二苯基膦基苯基）醚，4,5-双（二苯基膦基）-9,9-二甲基呫吨，环己基二苯基膦，1-1'-双（二苯基膦基）二茂铁，1,2-双（二苯基膦基） 醚，1,3-双（二苯基膦基）丙烷或三苯基膦。

公开(公告)号：KR1020100034256A

公开(公告)日：2010-04-01

申请号：KR1020080093293

申请日：2008-09-23

Applicant: 강원대학교산학협력단

Inventor： 박용광 ,  이태석 ,  이필호 ,  김현석 ,  어재명

IPC: C07C211/20 ,  C07C211/21 ,  C07C209/66

CPC classification number: C07C211/45 ,  C07C211/27 ,  C07C211/52 ,  C07C217/84 ,  C07C229/30 ,  C07C229/38 ,  C07C239/18 ,  C07D307/52

Abstract: PURPOSE: A method for preparing 1,3-butadiene-2-1-methyl amine derivatives is provided to synthesize a 1,3-butadiene-2-1-methyl amine derivative compound without separation of an imine compound formed through condensation reaction an aldehyde derivative and amine derivative. CONSTITUTION: A 1,3-butadiene-2-1-methyl amine derivative has a structure represented by chemical formula 1. In the chemical formula 1, A is (C1-C10) alkyl, (C3-C9) cyclo alkyl, (C6-C12) aryl, (C1-C10) alkoxycarbonyl, or (C3-C7) heteroaryl; B is (C6-C12) aryl, (C6-C12) ar (C1-C10) alkyl or (C6-C12) ar (C1-C10) alkoxy; and alkyl, cycloalkyl, aryl, alkoxycarbonyl, heteroaryl, aralkyl or aralkoxy of A and B can be substituted with at least one selected from (C1-C10) alkyl, (C1-C10) alkoxy, halogen or hydroxyl.

Abstract translation: 目的：提供1,3-丁二烯-2-甲基胺衍生物的制备方法，以合成1,3-丁二烯-2-甲基胺衍生物而不分离通过缩醛反应形成的亚胺化合物醛 衍生物和胺衍生物。 化学式1中，A为（C1-C10）烷基，（C3-C9）环烷基，（C6 -C 12）芳基，（C 1 -C 10）烷氧基羰基或（C 3 -C 7）杂芳基; B是（C 6 -C 12）芳基，（C 6 -C 12）芳基（C 1 -C 10）烷基或（C 6 -C 12）芳（C 1 -C 10）烷氧基; 并且A和B的烷基，环烷基，芳基，烷氧基羰基，杂芳基，芳烷基或芳烷氧基可以被选自（C1-C10）烷基，（C1-C10）烷氧基，卤素或羟基中的至少一种取代。