Reductive Friedel-Crafts process used for preparing tertiary compound, involves reacting amine compound with carbonyl compound in presence of organosilane, and first solvent to obtain tertiary amine compound, where organosilane is methyl silane, chlorodimethylsilane, triethylsilane
	YADAV N; KHAN J; HAZRA C K
	2023-07-28
专利权人	INDIAN INST TECHNOLOGY DELHI (IITD-C)
申请日期	2023-07-28
专利号	IN202311051075-A
成果简介	NOVELTY - Reductive Friedel-Crafts process involves reacting an amine compound (I) with a carbonyl compound (II) in the presence of an organosilane, and a first solvent at a temperature in a range of -25-80℃ to obtain the tertiary amine compound (III). USE - Reductive Friedel-Crafts process used for preparing tertiary compound, dimethylbenzene based compound, and diphenylacetic acid based compound (all claimed) for manufacturing pharmaceutically active compounds. ADVANTAGE - The method provides a step-economic, atomeconomic, and metal-free protocol utilizing cheap and commercially available starting materials for the reductive Friedel-Crafts alkylation of arenes or amines, and arylation of α-ketoacid to synthesize value-added products in high yield, and employs inexpensive reagents in a metal-free and catalyst-free condition to allow facile conversion of arenes and amines. DETAILED DESCRIPTION - Reductive Friedel-Crafts process involves reacting an amine compound of formula (I) with a carbonyl compound of formula (II) in the presence of an organosilane, and a first solvent at a temperature in a range of -25-80℃ to obtain the compound of formula (III). INDEPENDENT CLAIMS are included for: 1. a reductive Friedel-Crafts process for preparing a dimethylbenzene based compound of formula (VI), which involves: treating a mesitylene based compound of formula (IV) with a formaldehyde based compound of formula (V) in the presence of a silane compound, and a second solvent at a temperature in a range of -30 to 30℃ to obtain the dimethylbenzene based compound of formula (VI); and 2. a reductive Friedel-Crafts arylation for preparing diphenylacetic acid compound of formula (IX), which involves: arylating a phenylacetic acid based compound of formula (VII) using a benzene based compound of formula (VIII) in presence of a silicon reagent, a catalyst and a third solvent at a temperature in a range of -20 to 80℃ to obtain the diphenylacetic acid based compound of formula (IX). R1, R2=H, 1-12C alkyl, 2-12C alkenyl, 2-12C alkynyl, 6-15C aryl, 3-15C heteroaryl, or 3-15C heterocyclyl, where, 1-12C alkyl, 2-12C alkenyl, 2-12C alkynyl, 6-15C aryl, 3-15C heteroaryl, or 3-15C heterocyclyl is optionally substituted with substituents selected from halogen, cyano, hydroxyl, amino, nitro, 1-12C alkoxy, oxo, COOR', 1-12C alkyl, 6-15C aryl, or 6-15C 15 aryloxy, or R1and R2can be taken together to form 3-15C heteroaryl, or 3-15C heterocyclyl, where, 3-15C heteroaryl, or 3-15C heterocyclyl is optionally substituted with substituents selected from halogen, cyano, hydroxyl, amino, nitro, 1-12C alkoxy, oxo, 1-12C alkyl, 6-15C aryloxy, or optionally substituted 3-15C heterocyclyl, wherein, 1-12C alkyl is optionally substituted with 6-15C aryl; R' =H, 1-12C alkyl, 2-12C alkenyl, 2-12C alkynyl, or 6-15C aryl; R3, R4=H, 1-12C alkyl, 6-15C aryl, 3-15C carbocyclyl, 3-15C heteroaryl, or 3-15C heterocyclyl, where, 1-12C alkyl, 6-15C aryl, or 3-15C heteroaryl is optionally substituted with one or more substituents selected from halogen, cyano, hydroxyl, amino, nitro, COOR', 1-12C alkoxy, oxo, 1-12C alkyl, 25 or 6-15C aryloxy, or R3 and R4can be taken together to form a 3-15C carbocyclyl, C3- 15 heteroaryl, or 3-15C heterocyclyl, where, 3-15C carbocyclyl, 3-15C heteroaryl, or 3-15C heterocyclyl is optionally substituted with oxo, halogen, cyano, hydroxyl, amino, nitro, 1-12C alkoxy, 1-12C alkyl, or 6-15C aryloxy; R5= 1-12C alkyl, 6-15C aryl, 3-15C carbocyclyl, 3-15C heteroaryl, or 3-15C heterocyclyl, where 1-12C alkyl, 6-15C aryl, 3-15C carbocyclyl, 3-15C heteroaryl, or 3-15C heterocyclyl is optionally 5 substituted with one or more substituents selected from halogen, cyano, hydroxyl, amino, nitro, 1-12C alkoxy, oxo, 1-12C alkyl, COOR", or 6-15C aryloxy; R"=H, 1-12C alkyl, or 6-15C aryl. Full definitions are given in the DEFINITIONS (Full Definitions) Field.
IPC 分类号	C07B-041/06 ; C07B-041/08 ; C07B-061/00 ; C07C-209/24 ; C07C-211/03 ; C07C-211/09 ; C07C-211/35 ; C07C-045/46
国家	印度
专业领域	医药卫生
语种	英语
成果类型	专利
文献类型	科技成果
条目标识符	http://119.78.100.226:8889/handle/3KE4DYBR/21059
专题	中国科学院新疆生态与地理研究所
作者单位	INDIAN INST TECHNOLOGY DELHI (IITD-C)
推荐引用方式 GB/T 7714	YADAV N,KHAN J,HAZRA C K. Reductive Friedel-Crafts process used for preparing tertiary compound, involves reacting amine compound with carbonyl compound in presence of organosilane, and first solvent to obtain tertiary amine compound, where organosilane is methyl silane, chlorodimethylsilane, triethylsilane. IN202311051075-A[P]. 2023.

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