- Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids
-
A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.
- Deng, Tianning,Mazumdar, Wrickban,Ford, Russell L.,Jana, Navendu,Izar, Ragda,Wink, Donald J.,Driver, Tom G.
-
supporting information
p. 4456 - 4463
(2020/03/05)
-
- I(III)-catalyzed oxidative cyclization - Migration tandem reactions of unactivated anilines
-
An I(III)-catalyzed oxidative cyclization-migration tandem reaction using Selectfluor as the oxidant was developed that converts unactivated anilines into 3H-indoles is reported herein. The reaction requires as little as 1 mol % of the iodocatalyst and is mild, tolerating pyridine and thiophene functional groups, and the dependence of the diastereoselectivity of the process on the identity of the iodoarene or iodoalkane precatalyst suggests that the catalyst is present for the stereochemical determining C-N bond forming step.
- Deng, Tianning,Shi, Emily,Thomas, Elana,Driver, Tom G.
-
supporting information
p. 9102 - 9106
(2020/11/13)
-
- PIPERIDINYL-3-(ARYLOXY)PROPANAMIDES AND PROPANOATES
-
Disclosed are compounds of Formula (1), stereoisomers thereof, and pharmaceutically acceptable salts thereof, wherein L, r, s, R5, R6,R7, R9, R10, R11, R12, X1, X2, X3, X4, X13, and X14 are defined in the specification. This disclosure also relates to materials and methods for preparing compounds of Formula (1), to pharmaceutical compositions which contain them, and to their use for treating diseases, disorders, and conditions associated with SSTR4.
- -
-
Paragraph 0179; 0390-0391
(2019/09/18)
-
- Design, structure-activity relationship, and highly efficient asymmetric synthesis of 3-phenyl-4-benzylaminopiperidine derivatives as novel neurokinin-1 receptor antagonists
-
We synthesized a series of novel 3-phenyl-4-benzylaminopiperidine derivatives that were identified as potent tachykinin NK1 receptor antagonists by structural modification of the 3-benzhydrylpiperidone derivative through high-throughput screening. N-{2-[(3R,4S)-4-({2-Methoxy-5-[5-(trifluoromethyl)- 1Htetrazol-1-yl]benzyl}amino)-3-phenyl-1-piperidinyl]-2-oxoethyl}acetamide ((+)-39) was found to be one of the most potent tachykinin NK1 receptor antagonists with high metabolic stability. Highly efficient asymmetric synthesis of (+)-39 was achieved via dynamic kinetic resolution.
- Shirai, Junya,Yoshikawa, Takeshi,Yamashita, Masayuki,Yamamoto, Yasuharu,Kawamoto, Makiko,Tarui, Naoki,Kamo, Izumi,Hashimoto, Tadatoshi,Ikeura, Yoshinori
-
experimental part
p. 6430 - 6446
(2011/12/01)
-
- NK1 and NK3 antagonists
-
The invention is to a compound exhibiting neurokinin inhibitory properties, a pharmaceutical composition comprising same and a method of treatment for neurokinin-mediated conditions.
- -
-
Page/Page column 25
(2010/02/14)
-
