180340-57-2

Basic information

• Product Name: 5,6,7,8-TETRAHYDRO-4H-THIENO[3,2-B]AZEPINE
• Synonyms: 5,6,7,8-TETRAHYDRO-4H-THIENO[3,2-B]AZEPINE
• CAS NO: 180340-57-2
• Molecular Formula: C₈H₁₁NS
• Molecular Weight: 153.24
• Mol File: 180340-57-2.mol

Chemical Properties

• Boiling Point: 279.215 °C at 760 mmHg
• Flash Point: 122.665 °C
• Appearance: /
• Density: 1.098 g/cm³
• CAS DataBase Reference: 5,6,7,8-TETRAHYDRO-4H-THIENO[3,2-B]AZEPINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-TETRAHYDRO-4H-THIENO[3,2-B]AZEPINE(180340-57-2)
• EPA Substance Registry System: 5,6,7,8-TETRAHYDRO-4H-THIENO[3,2-B]AZEPINE(180340-57-2)

Safety Data

• Hazardous Substances Data: 180340-57-2(Hazardous Substances Data)

Upstream product

• 13292-87-0 dimethyl sulfide borane 
• 4751-61-5 4,6,7,8-Tetrahydro-4H-thieno[3,2-b]azepin-5-one 
• 137046-59-4 3-(3-Methoxycarbonyl-propionylamino)-thiophene-2-carboxylic acid methyl ester 
• 94252-22-9 6,7-dihydro-5H-benzo[b]thiophene-4-one O-tosyloxime 
• 13414-95-4 4-keto-4,5,6,7-tetrahydrothianaphthene 
• 137046-61-8 4H-thieno<3,2-b>azepine-5,8(6H,7H)-dione 
• 19995-19-8 4,5,6,7-tetrahydro-4-oxobenzo[b]thiophene oxime 

Downstream Products

• 384832-33-1 4-(4-Cyano-3-methylbenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine 
• 785040-42-8 [2-chloro-4-(5,6,7,8-tetrahydro-thieno[3,2-b]azepine-4-carbonyl)-benzyl]-carbamic acid tert-butyl ester 
• 180340-59-4 4-(4-Nitrobenzoyl)-4,5,6,7-tetrahydro-8H-thieno[3,2-b]-azepin-8-one 
• 180992-34-1 4-(2-chloro-4-aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine 
• 180992-32-9 2-chloro-4-(4-aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine 
• 180340-61-8 2-Chloro-4-(4-nitrobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine 
• 276867-99-3 6-(4-aminobenzoyl)pyrazolo[3,4-d]thieno[3,2-b]azepine 
• 180992-35-2 4,5,6,7-tetrahydro-4-(2-chloro-4-nitrobenzoyl)-8H-thieno[3,2-b]azepin-8-one 
• 180340-33-4 2,4,5,6-tetrahydro-2-methyl-6-(4-aminobenzoyl)pyrazolo[3,4-d]thieno[3,2-b]azepine 
• 180339-72-4 7-[(dimethylamino)methylene]-4,5,6,7-tetrahydro-4-(4-nitrobenzoyl)-8H-thieno [3,2-b]azepin-8-one 
• 276867-97-1 C₁₇H₁₄N₄O₃S 
• 276868-00-9 C₁₆H₁₃ClN₄OS 
• 276867-98-2 C₁₆H₁₁ClN₄O₃S 
• 180339-69-9 4-(2-Chloro-4-nitro-benzoyl)-7-[1-dimethylamino-meth-(E)-ylidene]-4,5,6,7-tetrahydro-thieno[3,2-b]azepin-8-one 

Relevant articles and documents

Ring-expansion reaction of oximes with aluminum reductants

The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH(OtBu)3, and (MeOCH 2CH2O)2AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl 3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.

Regioselective synthesis of heterocycles containing nitrogen neighboring an aromatic ring by reductive ring expansion using diisobutylaluminum hydride and studies on the reaction mechanism

(Chemical Equation Presented) A systematic investigation of the reductive ring-expansion reaction of cyclic ketoximes fused to aromatic ringswith diisobutylaluminum hydride (DIBALH) is described. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic heterocycles or tricyclic heterocycles containing nitrogen neighboring an aromatic ring, including indoline, 1,2,3,4,5,6-hexahydrobenz[b]azocine, 3,4-dihydro-2H-benzo[b] [1,4]oxazine, 2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine, 1,2,3,4,5,6- hexahydroazepino[3,2-b]-indole, 2,3,4,5-tetrahydro-1H-benzothieno[2,3-b]azepine, 2,3,4,5-tetrahydro-1H-benzothieno[3,2-b]-azepine, 5,6-dihydrophenanthridine, and 5,6,11,12-tetrahydrodibenz[b, f]azocine. The reaction mechanism leading to the rearrangement was investigated on the basis of the restricted Becke three-parameter plus Lee-Yang-Parr (B3LYP) density functional theory (DFT) with the 6-31G (d) basis set. It was found that the reaction proceeds through a three-centered transition state via a stepwise mechanism because the potential energy curve along the intrinsic reaction coordinate (IRC) had twomaxima (saddle points; TS1 and TS2) and the partial phenonium cation intermediate C. In addition to cyclic ketoximes fused to aromatic rings, the reactions of various cyclic and acyclic ketoximeswere examined to investigate preference of migrating group. It was found that themore electron-rich group migrated preferentially to give the corresponding secondary amines.

Non-peptide oxytocin agonists

The first non-peptide, low molecular weight agonists of the hormone oxytocin (OT) are reported. The most potent compound, 39, showed an EC 50 = 33 nM and was selective for the OT receptor. A library of compounds targeted to the vasopressin/oxytocin family of receptors was screened for activity at a cloned human oxytocin receptor using a reporter gene assay. Potency and selectivity were optimised to afford compound 39, EC50 = 33 nM. This series of compounds represents the first disclosed, non-peptide, low molecular weight agonists of the hormone oxytocin (OT).

Synthesis and Structure-Activity Relationships of 5,6,7,8-Tetrahydro-4H-thieno[3,2-b]azepine Derivatives: Novel Arginine Vasopressin Antagonists

A variety of novel heterocyclic compounds having thienoazepine, pyrroloazepine, furoazepine, and thienodiazepine skeletons were synthesized, most of which exhibited potent antagonism of [3H]-AVP specific binding in assays using rat liver (V1), rat kidney (V2), human platelet plasma membranes, and recombinant human CHO cells (V2), as well as antagonizing AVP-induced hypertension in rats (V1, intravenous) and showing a diuretic effect in rats (V2, oral). By detailed studies of the structure-activity relationships of these compounds, the thienoazepine derivative 1 was found to be a very potent combined V1 and V2 antagonist. After further pharmacological and toxicological evaluation as well as physical properties, the hydrochloride 2 (JTV-605) of compound 1 was selected for clinical studies as a potent AVP antagonist with a long duration of action.

Biphenyl vasopressin agonists

A compound of the formulae (I) or (II): wherein: Y is a moiety selected from NR or —(CH2)n; wherein R is hydrogen or (C1-C6) lower alkyl, and n is 1; represents: (1) a phenyl ring optionally substituted with one

The synthesis and vasopressin (AVP) antagonist activity of a novel series of N-Aroyl-2,4,5,6-tetrahydropyrazolo-[3,4-d]thieno[3,2-b]azepines

Synthesis and SAR of N-[4-[(4,5-dihydropyrazolo[3,4-d]thieno[3,2-b]azepin-6(2H)-yl)carbonyl]phenyl]be nzamides as arginine vasopressin (AVP) receptor antagonists are discussed. Potent orally active AVP receptor antagonists are produced when the benzamide moiety contains a phenyl group at the 2-position. Similar analogues of 4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepine and VPA-985 are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

Regioselective synthesis of several heterocyclic fused azepines using diisobutylaluminum hydride

5,6,7,8-Tetrahydrothieno[3,2-b]azepine,5,6,7,8-tetrahydro-1H-furo[3,2-b] azepine, and 1,4,5,6,7,8-hexahydropyrrolo[3,2-b]azepine were synthesized by the ring expansion reaction of heterocyclic fused cyclohexanone oximes with diisobutylaluminum hydride (DIBAH). The mechanism of the reaction was different from that of Beckmann rearrangement.

TRICYCLIC THIENO-AZEPINE VASOPRESSIN ANTAGONISTS

This invention relates to new bicyclic non-peptide vasopressin antagonists which are useful in treating conditions where decreased vasopressin levels are desired, such as in congestive heart failure, in disease conditions with excess renal water reabsorption and in conditions with increased vascular resistance and coronary vasoconstriction.